Total synthesis of (-)-cylindricine C

被引：76

作者：

Molander, GA ^{[1
]}

Rönn, M ^{[1
]}

机构：

[1] Univ Colorado, Dept Chem & Biochem, Boulder, CO 80309 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 14期

关键词：

D O I：

10.1021/jo990363l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(-)-Cylindricine C has been synthesized from commercially available (S)-(-)-1,2,4-butanetriol in 11 steps with an overall yield of 12%. The key step utilizes a CrCl2 reduction of an azide to form the corresponding amine with a subsequent double Michael addition to create the tricyclic skeleton of cylindricine from a monocyclic substrate.

引用

页码：5183 / 5187

页数：5

共 35 条

[1]

BAYLEY H, 1978, TETRAHEDRON LETT, P3633

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

BIARD, JF ;

GUYOT, S ;

ROUSSAKIS, C ;

VERBIST, JF ;

VERCAUTEREN, J ;

WEBER, JF ;

BOUKEF, K .

TETRAHEDRON LETTERS, 1994, 35 (17) :2691-2694

[3]

BLACKMAN A, COMMUNICATION

[4] CYLINDRICINE-A AND CYLINDRICINE-B, NOVEL ALKALOIDS FROM THE ASCIDIAN CLAVELINA-CYLINDRICA [J].

BLACKMAN, AJ ;

LI, CP ;

HOCKLESS, DCR ;

SKELTON, BW ;

WHITE, AH .

TETRAHEDRON, 1993, 49 (38) :8645-8656

[5]

BORJESSON L, 1995, J ORG CHEM, V60, P2989

[6]

BOSE AK, 1973, TETRAHEDRON LETT, P3937

[7] 1-AZASPIRO ANNELATION - SYNTHETIC APPROACH TO NATURALLY OCCURRING HETEROCYCLIC SPIRANES [J].

BRYSON, TA ;

WILSON, CA .

SYNTHETIC COMMUNICATIONS, 1976, 6 (07) :521-526

[8] TANDEM SN2-MICHAEL REACTIONS FOR THE PREPARATION OF SIMPLE 5-MEMBERED AND 6-MEMBERED-RING NITROGEN AND SULFUR HETEROCYCLES [J].

BUNCE, RA ;

PEEPLES, CJ ;

JONES, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1727-1733

[9]

COREY EJ, 1976, HETEROCYCLES, V5, P445

[10]

COREY EJ, 1976, TETRAHEDRON LETT, P3667

← 1 2 3 4 →