Angewandte
Chemie
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Scheme 6. Completion of the total synthesis of (ꢀ)-cribrostatin 4 (1):
a) [Pd(PPh3)2Cl2], Bu3SnH, AcOH, CH2Cl2; b) HCHO, NaBH3CN,
AcOH, MeOH; c) 10% Pd/C, HCO2H, MeOH; then air, MeOH, 76%
(for 3 steps); d) angeloyl chloride (27), toluene, 808C, 84%; e) salco-
mine, air, MeCN, 88%; f) SeO2, 1,4-dioxane, 908C, 62%, with 22%
recovered starting material; g) Dess–Martin periodinane, CH2Cl2;
h) Zn, MeOH, 87% (for 2 steps). Salcomine=N,N’-bis(salicylidene)
ethylenediaminecobalt(II) hydrate.
Keywords: alkaloids · antitumor agents · asymmetric synthesis ·
.
domino reactions · marine natural products
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Angew. Chem. Int. Ed. 2007, 46, 3962 –3965ꢀ 2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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