Abbreviated synthesis of the C3-C14 (substituted 1,7-dioxaspiro[5.5]undec-3-ene) system of okadaic acid

被引：17

作者：

Dounay, AB ^{[1
]}

Forsyth, CJ ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 03期

关键词：

D O I：

10.1021/ol9906615

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Described is a novel, concise, and flexible synthesis of the C3-C14 portion of okadaic acid. A substituted valerolactone (C3-C8) was prepared in three steps and cr-hydroxylated using Davis' oxaziridine, Conjugate addition of dimethylcuprate upon ynones derived from the C3-C8 lactones followed by intramolecular ketalization provided the C3-C14 fragment and revealed a significant role of the C7 alpha' ketone substituent upon the efficiency of spiroketalization.

引用

页码：451 / 453

页数：3

共 13 条

[11] Efficient synthesis of okadaic acid. 2. Synthesis of the C1-C14 domain and completion of the total synthesis [J].

Sabes, SF ;

Urbanek, RA ;

Forsyth, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2534-2542

[12] Efficient synthesis of okadaic acid. 1. Convergent assembly of the C15-C38 domain [J].

Urbanek, RA ;

Sabes, SF ;

Forsyth, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (11) :2523-2533

[13] AN EFFICIENT METHOD FOR THE ALKYNYLATION OF OXIRANES USING ALKYNYL BORANES [J].

YAMAGUCHI, M ;

HIRAO, I .

TETRAHEDRON LETTERS, 1983, 24 (04) :391-394

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