| Literature DB >> 22702243 |
Masaki Morita1, Go Hirai, Megumi Ohkubo, Hiroyuki Koshino, Daisuke Hashizume, Keiji Maruoka, Mikiko Sodeoka.
Abstract
The characteristic DEFGH-ring system of type B physalins has been synthesized by means of a one-pot procedure incorporating domino-type ring transformations. Unexpectedly, we found that introduction of an α-hydroxyester functionality at C17 in ring E allowed the key 7-endo oxy-Michael reaction to proceed. Originally this was thought to be an unfavored process. This afforded the desired caged ring system to be formed in a kinetically controlled manner. Consecutive treatment with AcOH at 100 °C furnished the DEFGH-ring system in one pot.Entities:
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Year: 2012 PMID： 22702243 DOI： 10.1021/ol301394b
Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005