Divergent total synthesis of penaresidin B and its straight side chain analogue

The divergent synthesis of penaresidin B and its straight side chain analogue was accomplished by constructing an azetidine ring via SN2 type cyclization of protected 2,3-syn-3,4-syn-4-amino-1,3-dihydroxyhept-6-en-2-yl mesylate and late-stage introduction of an alkyl side chain via olefin cross-meta...

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Bibliographic Details
Published in:Tetrahedron 2018-08, Vol.74 (35), p.4578-4591
Main Authors: Fujiwara, Tomoya, Hashimoto, Kazuki, Umeda, Masanori, Murayama, Saki, Ohno, Yuki, Liu, Bo, Nambu, Hisanori, Yakura, Takayuki
Format: Article
Language:English
Subjects:
Analogue
Azetidine
Olefin cross-metathesis reaction
Penaresidin
SN2 cyclization
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Summary:The divergent synthesis of penaresidin B and its straight side chain analogue was accomplished by constructing an azetidine ring via SN2 type cyclization of protected 2,3-syn-3,4-syn-4-amino-1,3-dihydroxyhept-6-en-2-yl mesylate and late-stage introduction of an alkyl side chain via olefin cross-metathesis of 4-allylazetidine with readily available terminal alkenes. This synthetic route would be useful to synthesize penaresidin side chain analogues. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.07.023