A Novel Enantioselective Synthesis of Cryptophycins Unit A from Rocher's Ester

被引：0

作者：

Mezrai, Abdelmoumin ^{[1
,2
]}

Mrah, Lahouari ^{[2
,3
]}

Khiati, Zoulikha ^{[3
]}

机构：

[1] Univ Tlemcen, Lab Organ Chem Nat Prod & Anal, POB 119, Tilimsen 13000, Algeria

[2] Ecole Super Genie Elect & Energet Oran, Chemin Vin 9, Oran, Algeria

[3] Univ Sci & Technol Oran Mohamed Boudiaf USTO MB, Fac Chim, Dept Genie Chim, Lab Synth Organ Phys Chim Biomol & Environm LSPBE, BP 1505 El Mnaouer, Oran 31000, Algeria

来源：

LETTERS IN ORGANIC CHEMISTRY | 2025年

关键词：

Cryptophycins; depsipeptide; cytotoxicity; antitumor agents; Reformatsky reaction; vinylogous Mukaiyama aldol reaction; ARENASTATIN-A; FRAGMENT-A; STEREOSELECTIVE-SYNTHESIS; CHEMOENZYMATIC SYNTHESIS; CONFORMATIONAL-ANALYSIS; BIOLOGICAL EVALUATION; ANTITUBULIN ACTIVITY; SECONDARY ALCOHOLS; ANTICANCER AGENTS; NATURAL-PRODUCTS;

D O I：

10.2174/0115701786356555241215053133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthesis of cryptophycin unit A in its enantiomerically pure form was achieved. In five steps, an enantiomeric mixture of unit A was initially prepared from trans-cinnamaldehyde. Subsequently, in its enantiomerically pure forms, unit A was prepared from Rocher's ester in six steps, involving an essential aldehyde (2R,3E)-2-methyl-4-phenylbut-3-enal. The final step of this process involved two different approaches: a Reformatsky reaction of an essential aldehyde with tertbutyl 4-bromocrotonate and the vinylogous Mukaiyama aldol reaction with O,O-Silyl ketene acetal in the presence of isopropyl alcohol and L-tryptophane-based B-phenyloxazaborolidinone, thereby resulting in the desired products in good overall yields and high enantioselectivities.

引用

页数：9