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Page 1: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 2: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 3: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 4: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 5: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 6: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 7: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 8: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 9: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 10: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 11: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 12: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 13: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 14: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 15: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 16: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 17: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 18: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 19: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 20: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 21: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 22: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 23: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 24: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 25: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 26: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 27: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 28: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 29: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 30: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 31: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn

NOH

Me

TBSO NOH

Me

TBSO

Me

OHMe

Me

OH

Me

N O

Me

Me

OHMe

TBSO

syn syn

N O

Me

Me

OHMe

TBSO

anti anti

N O

Me

Me

OHMe

TBSO

syn anti

N O

Me

Me

OHMe

TBSO

anti syn

Page 32: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 33: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 34: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 35: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 36: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 37: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 38: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 39: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 40: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 41: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn

✓ ✗ ✗

✓ ✗ ✗

✓ ✗ ✓✓ ✗ ✓✗ ✓ ✗

Page 42: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 43: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 44: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 45: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 46: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 47: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 48: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 49: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 50: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 51: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 52: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 53: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 54: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 55: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 56: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn
Page 57: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn

(+)-Δ9-cis-THC

(-)-Δ9-trans-THC

Page 58: ErickCarreira-2 - Princeton Universitychemlabs.princeton.edu/macmillan/wp-content/uploads/sites/6/Erick… · N OH Me TBSO N OH Me TBSO Me Me OH Me OH Me N O Me Me Me OH TBSO syn

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