A total synthesis of (+/-)-1-desoxyhypnophilin: using ring closing metathesis for the construction of cyclic enones

Authors
Harrowven, DC Lucas, MC Howes, PD
Citation
Dc. Harrowven et al., A total synthesis of (+/-)-1-desoxyhypnophilin: using ring closing metathesis for the construction of cyclic enones, TETRAHEDR L, 41(46), 2000, pp. 8985-8987
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
46
Year of publication
2000
Pages
8985 - 8987
Database
ISI
SICI code
0040-4039(20001111)41:46<8985:ATSO(U>2.0.ZU;2-6
Abstract
The paper describes the first total synthesis of (+/-)-1-desoxyhypnophilin, a linear triquinane isolated from the East African mushroom Lentinus crini tus which displays promising antimicrobial activity. The key strategic feat ure is a new cyclopentannulation method for appending cycloalkenones onto k etones involving sequential use of a ring closing metathesis reaction with a tertiary allylic alcohol and a PCC induced oxidative rearrangement. (C) 2 000 Elsevier Science Ltd. All rights reserved.