Synthesis of yomogin using a telescoped alpha-methylene-gamma-butyrolactone annelation procedure

TY - JOUR

T1 - Synthesis of yomogin using a telescoped alpha-methylene-gamma-butyrolactone annelation procedure

AU - Kitson, Russell R. A.

AU - McAllister, Graeme D.

AU - Taylor, Richard J. K.

PY - 2011/2/2

Y1 - 2011/2/2

N2 - A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.

AB - A novel and efficient synthetic route to the anti-cancer natural product yomogin has been developed using a Telescoped Intramolecular Michael-Olefination (TIMO) sequence as the key step. Two variants of the TIMO sequence have been used successfully: a two-step acylation approach using diethyl phosphonoacetic acid and a base-free variant using triphenylphosphoranylideneketene (Bestmann's ylide). The natural product, 3-oxodiplophyllin, was also prepared en route to yomogin. (C) 2010 Elsevier Ltd. All rights reserved.

KW - SESQUITERPENE LACTONES

KW - ARTEMISIA-PRINCEPS

KW - CELLS

KW - EUDESMANOLIDES

KW - TERPENOIDS

KW - INDUCTION

UR - http://www.scopus.com/inward/record.url?scp=78651107868&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.11.143

DO - 10.1016/j.tetlet.2010.11.143

M3 - Article

SN - 0040-4039

VL - 52

SP - 561

EP - 564

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -