The structural and synthetic implications of the biosynthesis of the calycanthaceous alkaloids, the communesins, and nomofungin

被引：105

作者：

May, Jeremy A. ^{[1
]}

Stoltz, Brian ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Arnold & Mable Beckman Lab Chem Synth, Pasadena, CA 91125 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 22期

关键词：

D O I：

10.1016/j.tet.2006.01.105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A comparison is made between the calycanthaceous alkaloids, nomofungin, and the communesins using structural and biosynthetic information from studies of the former to shed light on the structural ambiguity of the two latter species. Also, a novel biosynthetic approach for the communesins is presented that involves coupling of tryptamine with the ergot alkaloid aurantioclavine that is suitable for synthetic emulation. Preliminary synthetic studies and inter-mediates are reported. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5262 / 5271

页数：10

共 63 条

[31]

2-1

[32]

Li J, 2001, ANGEW CHEM INT EDIT, V40, P4770, DOI 10.1002/1521-3773(20011217)40:24<4770::AID-ANIE4770>3.0.CO

[33]

2-T

[34] ISOLATION AND STRUCTURE DETERMINATION OF DIAZONAMIDE-A AND DIAZONAMIDE-B, UNUSUAL CYTOTOXIC METABOLITES FROM THE MARINE ASCIDIAN DIAZONA-CHINENSIS [J].

LINDQUIST, N ;

FENICAL, W ;

VANDUYNE, GD ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2303-2304

[35]

Link JT, 1998, CHEMTECH, V28, P19

[36]

Lyle F. R., 1985, U.S. Patent, Patent No. [5 973 257, 5973257]

[37]

MASON SF, 1962, P CHEM SOC LONDON, P362

[38] Biomimetic approach to communesin B (a.k.a. nomofungin) [J].

May, JA ;

Zeidan, RK ;

Stoltz, BM .

TETRAHEDRON LETTERS, 2003, 44 (06) :1203-1205

[39] COMMUNESINS, CYTOTOXIC METABOLITES OF A FUNGUS ISOLATED FROM A MARINE ALGA [J].

NUMATA, A ;

TAKAHASHI, C ;

ITO, Y ;

TAKADA, T ;

KAWAI, K ;

USAMI, Y ;

MATSUMURA, E ;

IMACHI, M ;

ITO, T ;

HASEGAWA, T .

TETRAHEDRON LETTERS, 1993, 34 (14) :2355-2358

[40] 1,3-dipolar cycloaddition approach to indolic aza-analogues of cephalotaxine [J].

Nyerges, M ;

Rudas, M ;

Bitter, I ;

Toke, L ;

Szantay, C .

TETRAHEDRON, 1997, 53 (09) :3269-3280

← 1 2 3 4 5 6 7 →