Vallartanone B: Synthesis and related studies

Hirokazu Arimoto; Rieko Yokoyama; Kazuhiko Nakamura; Yasuaki Okumura; Daisuke Uemura

doi:10.1016/0040-4020(96)00852-6

Vallartanone B: Synthesis and related studies

Hirokazu Arimoto, Rieko Yokoyama, Kazuhiko Nakamura, Yasuaki Okumura, Daisuke Uemura

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

10 Citations (Scopus)

Abstract

The synthesis of vallartanone B, a γ-pyrone-containing polypoprionate from the marine mollusc Siphonaria maura, is described. A γ-pyrone moiety, which was constructed by PPh₃-CCl₄ cyclization of a β-triketone, and a C1-C6 segment were joined by a Sn(OTf)₂ aldol reaction and converted to vallartanone B. This synthesis allows for revision of the stereochemistry at C8. A conformational analysis was performed using PM3 to examine the proposed interpretation of its CD spectrum.

Original language	English
Pages (from-to)	13901-13908
Number of pages	8
Journal	Tetrahedron
Volume	52
Issue number	44
DOIs	https://doi.org/10.1016/0040-4020(96)00852-6
Publication status	Published - 1996 Oct 28
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

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10.1016/0040-4020(96)00852-6

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title = "Vallartanone B: Synthesis and related studies",

abstract = "The synthesis of vallartanone B, a γ-pyrone-containing polypoprionate from the marine mollusc Siphonaria maura, is described. A γ-pyrone moiety, which was constructed by PPh3-CCl4 cyclization of a β-triketone, and a C1-C6 segment were joined by a Sn(OTf)2 aldol reaction and converted to vallartanone B. This synthesis allows for revision of the stereochemistry at C8. A conformational analysis was performed using PM3 to examine the proposed interpretation of its CD spectrum.",

author = "Hirokazu Arimoto and Rieko Yokoyama and Kazuhiko Nakamura and Yasuaki Okumura and Daisuke Uemura",

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T1 - Vallartanone B

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AU - Arimoto, Hirokazu

AU - Yokoyama, Rieko

AU - Nakamura, Kazuhiko

AU - Okumura, Yasuaki

AU - Uemura, Daisuke

PY - 1996/10/28

Y1 - 1996/10/28

N2 - The synthesis of vallartanone B, a γ-pyrone-containing polypoprionate from the marine mollusc Siphonaria maura, is described. A γ-pyrone moiety, which was constructed by PPh3-CCl4 cyclization of a β-triketone, and a C1-C6 segment were joined by a Sn(OTf)2 aldol reaction and converted to vallartanone B. This synthesis allows for revision of the stereochemistry at C8. A conformational analysis was performed using PM3 to examine the proposed interpretation of its CD spectrum.

AB - The synthesis of vallartanone B, a γ-pyrone-containing polypoprionate from the marine mollusc Siphonaria maura, is described. A γ-pyrone moiety, which was constructed by PPh3-CCl4 cyclization of a β-triketone, and a C1-C6 segment were joined by a Sn(OTf)2 aldol reaction and converted to vallartanone B. This synthesis allows for revision of the stereochemistry at C8. A conformational analysis was performed using PM3 to examine the proposed interpretation of its CD spectrum.

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EP - 13908

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 44

ER -

Vallartanone B: Synthesis and related studies

Abstract

ASJC Scopus subject areas

UN SDGs

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