Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cylindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C).

被引：66

作者：

Pearson, WH

Barta, NS

Kampf, JW

机构：

[1] Department of Chemistry, University of Michigan, Ann Arbor

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(97)00632-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tin-lithium exchange of 13 with n-BuLi produced the 2-azapentadienyl anion 6 (R = CH3), which participated in a [pi 4s+pi 2s] cycloaddition reaction with phenyl vinyl sulfide to afford the spirocyclic pyrrolidine 14, which as coverted to 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C) 17 by a sequence of steps involving oxidative cleavage of the propenyl side-chain, intramolecular reductive amination, and desulfurization. (C) 1997 Elsevier Science Ltd.

引用

页码：3369 / 3372

页数：4

共 20 条

[1]

[Anonymous], 1984, ASYMMETRIC SYNTHESIS

[2]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[3] LEPADIFORMINE, A NEW MARINE CYTOTOXIC ALKALOID FROM CLAVELINA-LEPADIFORMIS MULLER [J].