An approach toward the total synthesis of subergorgic acid

Ireland–Claisen rearrangement of a substituted alkenyl cyclopentanecarboxylate provided a monocyclic isomer containing the proper stereochemistry for four of the five stereogenic centers in subergorgic acid. Efforts to construct the additional rings in the molecule were thwarted as a result of steri...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 64; no. 23; pp. 5482 - 5490
Main Authors Gilbert, John C., Yin, Jiandong
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.06.2008
Elsevier
Subjects
Chemistry
Chemistry, Organic
Diastereoselectivity
Facial selectivity
Ireland–Claisen rearrangement
Physical Sciences
Science & Technology
Subergorgic acid
Subergorgic acid
Facial selectivity
Ireland–Claisen rearrangement
Diastereoselectivity
ENOLATE CLAISEN REARRANGEMENT
ALPHA-ALKYNONE CYCLIZATION
subergorgic acid
Ireland-Claisen rearrangement
(+/-)-SUBERGORGIC ACID
ESTER ENOLATE
diastereoselectivity
RAC-MODHEPHENE
STEREOCHEMICAL CONTROL
RADICAL CYCLIZATION
ORGANIC-COMPOUNDS
ALKYLIDENECARBENES
STEREOSELECTIVE-SYNTHESIS
facial selectivity
Online AccessGet full text

Cover

More Information
Summary:Ireland–Claisen rearrangement of a substituted alkenyl cyclopentanecarboxylate provided a monocyclic isomer containing the proper stereochemistry for four of the five stereogenic centers in subergorgic acid. Efforts to construct the additional rings in the molecule were thwarted as a result of steric and other factors. The results provide insights regarding the Ireland–Claisen rearrangement in five-membered ring systems. The formation of spiro-compounds from sterically and stereoelectronically demanding systems as reported herein has the potential to serve as a general strategy for the synthesis of such sub-units in both natural and unnatural products. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.04.005