Towards Stereoselective Synthesis of the C(31) - C(39) and C(20) - C(27) Fragments of Phorboxazole A

被引：9

作者：

Raju, Kammari Bal ^{[1
]}

Kumar, Bejjanki Naveen ^{[1
]}

Kumar, Bandari Sampath ^{[1
]}

Nagaiah, Kommu ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ & Biomol Chem Div, Hyderabad 500076, Andhra Pradesh, India

来源：

HELVETICA CHIMICA ACTA | 2015年 / 98卷 / 03期

关键词：

Phorboxazole A; D-Mannitol; Crimmins aldol reaction; Aldol reaction; L-proline-catalyzed; Cytotoxic activity; CROSS-ALDOL REACTION; SPONGE PHORBAS SP; RING-CLOSING METATHESIS; ASYMMETRIC-SYNTHESIS; CONVERGENT SYNTHESIS; NATURAL-PRODUCTS; MARINE SPONGE; ABSOLUTE-CONFIGURATION; TITANIUM TETRACHLORIDE; CARBONYL-COMPOUNDS;

D O I：

10.1002/hlca.201400279

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A (1) was achieved from commercially available and inexpensive D-mannitol. Crimmins aldol reaction and a decarboxylative Claisen-type reaction are the key steps for the C(31)-C(39) fragment, and L-proline-catalyzed aldol reaction, Sharpless asymmetric epoxidation, and epoxide ring opening reaction with Gilman's reagent are the key steps for the C(20)-C(27) fragment of phorboxazole.

引用

页码：386 / 398

页数：13

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