Stereoselective synthesis of (E)-beta-tributylstannyl-alpha,beta-unsaturated ketones: Construction of a key intermediate for the total synthesis of zoanthamine

Thomas Eiland Nielsen; David Ackland Tanner

Stereoselective synthesis of (E)-beta-tributylstannyl-alpha,beta-unsaturated ketones: Construction of a key intermediate for the total synthesis of zoanthamine

Thomas Eiland Nielsen
, David Ackland Tanner

Department of Chemistry

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

(E)-beta-Trialkylstannyl-alpha,beta-unsaturated ketones are readily available from secondary propargylic alcohols via a two-step sequence involving highly regio- and stereoselective Pd(0)-catalyzed hydrostannation followed by mild oxidation (TPAP). The methodology has been applied to the synthesis of enantiomerically pure enone 12 which is a key intermediate for the total synthesis of zoanthamine, a structurally complex marine natural product.

Original language	English
Journal	Journal of organic chemistry
Volume	67
Issue number	18
Pages (from-to)	6366-6371
ISSN	0022-3263
Publication status	Published - 2002

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title = "Stereoselective synthesis of (E)-beta-tributylstannyl-alpha,beta-unsaturated ketones: Construction of a key intermediate for the total synthesis of zoanthamine",

abstract = "(E)-beta-Trialkylstannyl-alpha,beta-unsaturated ketones are readily available from secondary propargylic alcohols via a two-step sequence involving highly regio- and stereoselective Pd(0)-catalyzed hydrostannation followed by mild oxidation (TPAP). The methodology has been applied to the synthesis of enantiomerically pure enone 12 which is a key intermediate for the total synthesis of zoanthamine, a structurally complex marine natural product.",

author = "Nielsen, \{Thomas Eiland\} and Tanner, \{David Ackland\}",

year = "2002",

language = "English",

volume = "67",

pages = "6366--6371",

journal = "Journal of organic chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

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TY - JOUR

T1 - Stereoselective synthesis of (E)-beta-tributylstannyl-alpha,beta-unsaturated ketones: Construction of a key intermediate for the total synthesis of zoanthamine

AU - Nielsen, Thomas Eiland

AU - Tanner, David Ackland

PY - 2002

Y1 - 2002

N2 - (E)-beta-Trialkylstannyl-alpha,beta-unsaturated ketones are readily available from secondary propargylic alcohols via a two-step sequence involving highly regio- and stereoselective Pd(0)-catalyzed hydrostannation followed by mild oxidation (TPAP). The methodology has been applied to the synthesis of enantiomerically pure enone 12 which is a key intermediate for the total synthesis of zoanthamine, a structurally complex marine natural product.

AB - (E)-beta-Trialkylstannyl-alpha,beta-unsaturated ketones are readily available from secondary propargylic alcohols via a two-step sequence involving highly regio- and stereoselective Pd(0)-catalyzed hydrostannation followed by mild oxidation (TPAP). The methodology has been applied to the synthesis of enantiomerically pure enone 12 which is a key intermediate for the total synthesis of zoanthamine, a structurally complex marine natural product.

M3 - Journal article

SN - 0022-3263

VL - 67

SP - 6366

EP - 6371

JO - Journal of organic chemistry

JF - Journal of organic chemistry

IS - 18

ER -

Stereoselective synthesis of (E)-beta-tributylstannyl-alpha,beta-unsaturated ketones: Construction of a key intermediate for the total synthesis of zoanthamine

Abstract

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