Synthesis and structure revision of the C43-C67 part of amphidinol 3

Makoto Ebine; Mitsunori Kanemoto; Yoshiyuki Manabe; Yosuke Konno; Ken Sakai; Nobuaki Matsumori; Michio Murata; Tohru Oishi

doi:10.1021/ol401176a

Synthesis and structure revision of the C43-C67 part of amphidinol 3

Makoto Ebine, Mitsunori Kanemoto, Yoshiyuki Manabe, Yosuke Konno, Ken Sakai, Nobuaki Matsumori, Michio Murata, Tohru Oishi

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of AM3 was revised from R to S.

Original language	English
Pages (from-to)	2846-2849
Number of pages	4
Journal	Organic letters
Volume	15
Issue number	11
DOIs	https://doi.org/10.1021/ol401176a
Publication status	Published - Jun 7 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol401176a

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AU - Ebine, Makoto

AU - Kanemoto, Mitsunori

AU - Manabe, Yoshiyuki

AU - Konno, Yosuke

AU - Sakai, Ken

AU - Matsumori, Nobuaki

AU - Murata, Michio

AU - Oishi, Tohru

PY - 2013/6/7

Y1 - 2013/6/7

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AB - Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of AM3 was revised from R to S.

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Synthesis and structure revision of the C43-C67 part of amphidinol 3

Abstract

All Science Journal Classification (ASJC) codes

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