A remarkable ring contraction en route to the chartelline alkaloids

被引：58

作者：

Baran, PS ^{[1
]}

Shenvi, RA ^{[1
]}

Mitsos, CA ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 24期

关键词：

D O I：

10.1002/anie.200500522

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Weinheim (Chemical Equation Presented) One-of-a-kind. A bromine-induced rearrangement has been designed for the formation of the spiro-β-lactam ring present in the structurally unique chartelline alkaloids (see picture of chartelline A). This method is used in combination with others to provide rapid access to the carbocyclic skeletons of the chartelline, securine, and securamine alkaloids. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：3714 / 3717

页数：4

相关论文

共 38 条

[11] SYNTHESIS OF (-)-VINDOLINE [J].

FELDMAN, PL ;

RAPOPORT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1603-1604

[12] CHEMICAL STUDIES OF MARINE-BACTERIA - DEVELOPING A NEW RESOURCE [J].

FENICAL, W .

CHEMICAL REVIEWS, 1993, 93 (05) :1673-1683

[13] FACILE DESULFURIZATION OF CYCLIC THIOUREAS BY HYDROGEN-PEROXIDE IN ACETIC-ACID [J].

GRIVAS, S ;

RONNE, E .

ACTA CHEMICA SCANDINAVICA, 1995, 49 (03) :225-229

[14] Total synthesis of anti-microtubule diketopiperazine derivatives: Phenylahistin and aurantiamine [J].

Hayashi, Y ;

Orikasa, S ;

Tanaka, K ;

Kanoh, K ;

Kiso, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8402-8405

[15]

Joule J. A., 2000, Heterocyclic Chemistry, V4th, P589

[16] Synthesis and biological activities of phenylahistin derivatives [J].

Kanoh, K ;

Kohno, S ;

Katada, J ;

Takahashi, J ;

Uno, I ;

Hayashi, Y .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (07) :1451-1457

[17] Efficient construction of the securine A carbon skeleton [J].

Korakas, P ;

Chaffee, S ;

Shotwell, JB ;

Duque, P ;

Wood, JL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (33) :12054-12057

[18]

KORAKAS P, 2003, THESIS YALE U

[19]

LIN X, 2002, THESIS PENNSYLVANIA

[20] Model studies on total synthesis of the chartellines, spirocyclic β-lactam alkaloids from a marine bryozoan [J].

Lin, XC ;

Weinreb, SM .

TETRAHEDRON LETTERS, 2001, 42 (14) :2631-2633

← 1 2 3 4 →