Open AccessSynthesis of Squamostanal-A
Author(s) -
Hiroyuki Konno,
Hidefumi Makabe,
Akira Tanaka,
Takayuki Oritani
Publication year - 1996
Publication title -
bioscience biotechnology and biochemistry
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 0.509
H-Index - 116
eISSN - 1347-6947
pISSN - 0916-8451
DOI - 10.1271/bbb.60.526
Subject(s) - computer science
The first synthesis of squamostanal-A (1), separated as a degradation product of tetrahydrofuranic acetogenins, is described. Iodide 7, which corresponds to the latent aldehyde moiety of 1, was prepared through a 2-step sequence from 13-[tetrahydropyran-2'- yloxy]-2-tridecyn-l-ol (5). The NaHMDS-based coupling reaction of 7 with γ-lactone 8 gave compound 9, which by a 3-step sequence, was coverted to 1.
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