An efficient and stereoselective construction of the core structure of the manzamines via an intramolecular Michael reaction.

被引:21
作者
Brands, KMJ [1 ]
DiMichele, LM [1 ]
机构
[1] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA
关键词
D O I
10.1016/S0040-4039(98)00019-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A strategically functionalized tricyclic subunit of the manzamines was efficiently synthesized with complete stereochemical control using a combination of an intramolecular Michael reaction of a pyroglutamic acid derivative and a hydrogenation. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1677 / 1680
页数:4
相关论文
共 15 条
  • [1] An approach to the manzamine alkaloids modelled on a biogenetic theory
    Baldwin, JE
    Bischoff, L
    Claridge, DW
    Heupel, FA
    Spring, DR
    Whitehead, RC
    [J]. TETRAHEDRON, 1997, 53 (06) : 2271 - 2290
  • [2] AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL
    BALDWIN, JE
    MIRANDA, T
    MOLONEY, M
    HOKELEK, T
    [J]. TETRAHEDRON, 1989, 45 (23) : 7459 - 7468
  • [3] COREY EJ, 1972, TETRAHEDRON LETT, P3769
  • [4] TITANIUM ENOLATES FROM PYROGLUTAMATES - EXCLUSIVE FORMATION OF 4-ALPHA ALDOL ADDUCTS
    DIKSHIT, DK
    BAJPAI, SN
    [J]. TETRAHEDRON LETTERS, 1995, 36 (18) : 3231 - 3232
  • [5] Four new bioactive manzamine-type alkaloids from the Philippine marine sponge Xestospongia ashmorica
    Edrada, RA
    Proksch, P
    Wray, V
    Witte, L
    Muller, WEG
    VanSoest, RWM
    [J]. JOURNAL OF NATURAL PRODUCTS, 1996, 59 (11): : 1056 - 1060
  • [6] SYNTHESIS OF ENANTIOMERICALLY PURE 4-SUBSTITUTED GLUTAMIC ACIDS AND PROLINES - GENERAL ALDOL REACTION OF PYROGLUTAMATE LACTAM LITHIUM ENOLATE MEDIATED BY ET(2)O-CENTER-DOT-BF3
    EZQUERRA, J
    PEDREGAL, C
    YRURETAGOYENA, B
    RUBIO, A
    CARRENO, MC
    ESCRIBANO, A
    RUANO, JLG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) : 2925 - 2930
  • [7] STEREOSELECTIVE DOUBLE ALKYLATION OF ETHYL N-BOC-PYROGLUTAMATE
    EZQUERRA, J
    PEDREGAL, C
    RUBIO, A
    VAQUERO, JJ
    MATIA, MP
    MARTIN, J
    DIAZ, A
    NAVIO, JLG
    DEETER, JB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4327 - 4331
  • [8] STEREOSELECTIVE REACTIONS OF LITHIUM ENOLATES DERIVED FROM N-BOC PROTECTED PYROGLUTAMIC ESTERS
    EZQUERRA, J
    PEDREGAL, C
    RUBIO, A
    YRURETAGOYENA, B
    ESCRIBANO, A
    SANCHEZFERRANDO, F
    [J]. TETRAHEDRON, 1993, 49 (38) : 8665 - 8678
  • [9] The structure and biogenetic origin of (-)halicyclamine B from a Xestospongia sponge
    Harrison, B
    Talapatra, S
    Lobkovsky, E
    Clardy, J
    Crews, P
    [J]. TETRAHEDRON LETTERS, 1996, 37 (51) : 9151 - 9154
  • [10] HETEROCYCLES IN ASYMMETRIC-SYNTHESIS .1. CONSTRUCTION OF THE CHIRAL BUILDING-BLOCKS FOR ENANTIOSELECTIVE ALKALOID SYNTHESIS VIA AN ASYMMETRIC INTRAMOLECULAR MICHAEL REACTION
    HIRAI, Y
    TERADA, T
    YAMAZAKI, T
    MOMOSE, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (04): : 509 - 516