Towards a total synthesis of the manadomanzamine alkaloids: the first asymmetric construction of the pentacyclic indole core

S. M. Allin; L. J. Duffy; P. C. B. Bulman Page; V. McKee; M. J. McKenzie

doi:10.1016/j.tetlet.2007.05.030

Towards a total synthesis of the manadomanzamine alkaloids: the first asymmetric construction of the pentacyclic indole core

S. M. Allin, L. J. Duffy, P. C. B. Bulman Page, V. McKee, M. J. McKenzie

Chemistry of Materials and Catalysis

Research output: Contribution to journal › Article › peer-review

21 Citations (Scopus)

Abstract

We report a highly diastereoselective approach for the synthesis of the pentacyclic indole core of the manadomanzamine alkaloid skeleton, with complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10, and 24, from a readily available chiral template. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4711-4714
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	27
DOIs	https://doi.org/10.1016/j.tetlet.2007.05.030
Publication status	Published - 2 Jul 2007

Keywords

HIGHLY STEREOSELECTIVE-SYNTHESIS
NATURAL-PRODUCT SYNTHESIS
DERIVATIVES
ENANTIOMERS
PYRROLOISOQUINOLINE RING-SYSTEM
FACILE
TEMPLATES

Access to Document

10.1016/j.tetlet.2007.05.030

Cite this

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title = "Towards a total synthesis of the manadomanzamine alkaloids: the first asymmetric construction of the pentacyclic indole core",

abstract = "We report a highly diastereoselective approach for the synthesis of the pentacyclic indole core of the manadomanzamine alkaloid skeleton, with complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10, and 24, from a readily available chiral template. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.",

keywords = "HIGHLY STEREOSELECTIVE-SYNTHESIS, NATURAL-PRODUCT SYNTHESIS, DERIVATIVES, ENANTIOMERS, PYRROLOISOQUINOLINE RING-SYSTEM, FACILE, TEMPLATES",

author = "Allin, {S. M.} and Duffy, {L. J.} and {Bulman Page}, {P. C. B.} and V. McKee and McKenzie, {M. J.}",

year = "2007",

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doi = "10.1016/j.tetlet.2007.05.030",

language = "English",

volume = "48",

pages = "4711--4714",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "27",

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TY - JOUR

T1 - Towards a total synthesis of the manadomanzamine alkaloids: the first asymmetric construction of the pentacyclic indole core

AU - Allin, S. M.

AU - Duffy, L. J.

AU - Bulman Page, P. C. B.

AU - McKee, V.

AU - McKenzie, M. J.

PY - 2007/7/2

Y1 - 2007/7/2

N2 - We report a highly diastereoselective approach for the synthesis of the pentacyclic indole core of the manadomanzamine alkaloid skeleton, with complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10, and 24, from a readily available chiral template. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

AB - We report a highly diastereoselective approach for the synthesis of the pentacyclic indole core of the manadomanzamine alkaloid skeleton, with complete control over the relative and absolute stereochemistries at the three contiguous stereocentres at ring positions 1, 10, and 24, from a readily available chiral template. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

KW - HIGHLY STEREOSELECTIVE-SYNTHESIS

KW - NATURAL-PRODUCT SYNTHESIS

KW - DERIVATIVES

KW - ENANTIOMERS

KW - PYRROLOISOQUINOLINE RING-SYSTEM

KW - FACILE

KW - TEMPLATES

U2 - 10.1016/j.tetlet.2007.05.030

DO - 10.1016/j.tetlet.2007.05.030

M3 - Article

VL - 48

SP - 4711

EP - 4714

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 27

ER -