SYNTHESIS OF SQUAMOSTANAL-A

Authors
KONNO H MAKABE H TANAKA A ORITANI T
Citation
H. Konno et al., SYNTHESIS OF SQUAMOSTANAL-A, Bioscience, biotechnology, and biochemistry, 60(3), 1996, pp. 526-527
Citations number
12
Categorie Soggetti
Biology,Agriculture,"Biothechnology & Applied Migrobiology","Food Science & Tenology
Journal title
Bioscience, biotechnology, and biochemistry → ACNP
ISSN journal
09168451
Volume
60
Issue
3
Year of publication
1996
Pages
526 - 527
Database
ISI
SICI code
0916-8451(1996)60:3<526:SOS>2.0.ZU;2-O
Abstract
The first synthesis of squamostanal-A (1), separated as a degradation product of tetrahydrofuranic acetogenins, is described. Iodide 7, whic h corresponds to the latent aldehyde moiety of 1, was prepared through a 2-step sequence from 13-[tetrahydropyran-2'-yloxy]-2-tridecyn-1-ol (5). The NaHMDS-based coupling reaction of 7 with gamma-lactone 8 gave compound 9, which by a 3-step sequence, was coverted to 1.