Synthesis of a Mexican bean beetle azamacrolide allomone via a novel lactam to lactone ring expansion

被引：13

作者：

Gribble, GW

Silva, RA

机构：

[1] Department of Chemistry, Dartmouth College, Hanover

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 13期

关键词：

D O I：

10.1016/0040-4039(96)00234-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Mexican bean beetle (Epilachna varivestis) defensive secretion azamacrolide 1 has been synthesized via the novel ring expansion of N-hydroxyethyl lactam 12, which was prepared in seven steps from cyclooctanone (6).

引用

页码：2145 / 2148

页数：4

共 20 条

[1] AZAMACROLIDES - A FAMILY OF ALKALOIDS FROM THE PUPAL DEFENSIVE SECRETION OF A LADYBIRD BEETLE (EPILACHNA-VARIVESTIS)
ATTYGALLE, AB
MCCORMICK, KD
BLANKESPOOR, CL
EISNER, T
MEINWALD, J
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (11) : 5204 - 5208
[2] BIOSYNTHESIS OF A DEFENSIVE INSECT ALKALOID - EPILACHNENE FROM OLEIC-ACID AND SERINE
ATTYGALLE, AB
BLANKESPOOR, CL
EISNER, T
MEINWALD, J
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (26) : 12790 - 12793
[3] AN EFFICIENT SYNTHESIS OF LARGE RING ACETYLENES
BOIVIN, J
HUPPE, S
ZARD, SZ
[J]. TETRAHEDRON LETTERS, 1995, 36 (32) : 5737 - 5740
[4] TRANSLACTONIZATION ROUTE TO MACROCYCLIC LACTONES
COREY, EJ
BRUNELLE, DJ
NICOLAOU, KC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (22) : 7359 - 7360
[5] SYNTHESIS OF THE ALKALOIDS HOPROMINE, HOPROMINOL AND HOPROMALINOL, USING TRANSAMIDATION METHODS
CROMBIE, L
HAIGH, D
JONES, RCF
MATZIN, AR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (17): : 2055 - 2068
[6] Elsinger F., 1973, ORG SYNTH, V5, P76
[7] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION
INANAGA, J
HIRATA, K
SAEKI, H
KATSUKI, T
YAMAGUCHI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) : 1989 - 1993
[8] KOCH T, 1995, SYNTHESIS-STUTTGART, P251
[9] ZIP-REACTION - NEW METHOD FOR SYNTHESIS OF MACROCYCLIC POLYAMINOLACTAMS
KRAMER, U
GUGGISBERG, A
HESSE, M
SCHMID, H
[J]. HELVETICA CHIMICA ACTA, 1978, 61 (04) : 1342 - 1352
[10] MEINWALD J, COMMUNICATION

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