THE SYNTHESIS OF (+/-)-ISOPTYCHANOLIDE BY APPLICATION OF THE ALPHA-ALKYNONE CYCLIZATION

被引：14

作者：

SOLAJA, B ^{[1
]}

HUGUET, J ^{[1
]}

KARPF, M ^{[1
]}

DREIDING, AS ^{[1
]}

机构：

[1] UNIV ZURICH, INST ORGAN CHEM, WINTERTHURERSTR 190, CH-8057 ZURICH, SWITZERLAND

来源：

TETRAHEDRON | 1987年 / 43卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(01)87670-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of racemic isopytychanolide (2), a stereoisomer of natural ptychanolide (1), which differs in the configuration of the oxirane function, is reported. The key steps were an .alpha.-alkinone cyclisation (5 .fwdarw. 4, gas phase flow thermolysis at 620.degree.), a stereoselective exo allylation of the enolate (F) derived upon desoxygenation and reduction of the enol ether 10, elaboration of the two substituents at C(3) of the resulting 11 to afford the enol lactone 3. Epoxidation of the double bond of 3 took place from the side of C(2) (and not of C(4)), so that isophychanolide (2) was formed. The configurations of all stereocentres in 2 were determined by an X-ray analysis.

引用

页码：4875 / 4886

页数：12

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