Highlights from the Synthesis of Gibberellins:

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HO 2C HO * CH 3 OH mevalonic acid (MVA) DMAPP Dimethylallyl pyrophosphate OPP IPP Isopentenyl pyrophosphate OPP 11-gibberellin-biosynthesis2 2/5/04 12:30 PM Gibberellin Biosynthesis: Stage A Stage A H 3C H H3C CH3 IPP IPP OPP GPP * * H * * ent-kaur-16-ene FPP H 3C H H 3C CH 3 H OPP OPP ent-CCP ent-copalyl pyrophosphate OPP GGPP geranyl-geranyl pyrophosphate
H 3C H H 3C CH 3 12-biosynthesis3.cdx 2/5/04 10:11 PM H Gibberellin Biosynthesis: ent-CCP to ent-kaurene OPP ent-CCP ent-copalyl pyrophosphate H a H H 5S H 5R H 4 OPP H 3C H H 3C CH 3 H ent-kaur-16-ene H5R H5S H a H H 4 H 5R H 5S H H5R H5S H a H a H H 4 H
Page 1 and 2: Highlights from the Synthesis of Gi
Page 3 and 4: HO OC CH 3 O H A Brief History of G
Page 5 and 6: HO 2 3 11 12 1 O OC 19 5 H 9 6 H 8
Page 7: HO 2C HO Me OH mevalonic acid (MVA)
Page 11 and 12: H HO2C Enz H 3C H 3C CH 3 O H H H e
Page 13 and 14: HO GA 3 OC CH 3 O OH H H Gibberelli
Page 15 and 16: AcO OC Me O H CO 2Me BH 3 18-GA-C11
Page 17 and 18: MOMO MOMO MOMO acyloin rearrangemen
Page 19 and 20: MOMO OC CH 3 H OC CH 3 Li/NH 3 tBuO
Page 21 and 22: HO OC Me Zn O H 90% F 3C H CO 2Me T
Page 23 and 24: Cl THPO O O Contraction of B-Ring;
Page 25 and 26: O Alternative Route to Key Tricycli
Page 27 and 28: MeO HO 2C MeO TFA MeO CO 2Me 35% CO
Page 29 and 30: PhOCO OC 1) DBU 2) H 2O, H + 3) TMS
Page 31 and 32: Me SEMO MOMOH 2C CN CO 2Me H Me O 3
Page 33 and 34: CO 2Me O OMe H EtO2C MeO 52% OC O H
Page 35 and 36: MeO 2C Me H Me H (±)- from synthes
Page 37 and 38: O O H O O Three Routes to Bicycle:
Page 39 and 40: AcO HO2C Proposed Biomimmetic Synth
Page 41 and 42: AcO 75% OC O H antheridic acid OMe
Page 43 and 44: H MeO2C H O CO2Me 1) NaOMe CO2Me2)
Page 45 and 46: H H MeO O Me Cl H OH O Me OH OMs CO

Highlights from the Synthesis of Gibberellins:

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