Synthetic studies on (+)-ophiobolin A: Asymmetric synthesis of the spirocyclic CD-ring moiety

Naoyoshi Noguchi; Masahisa Nakada

doi:10.1021/ol060437x

Synthetic studies on (+)-ophiobolin A: Asymmetric synthesis of the spirocyclic CD-ring moiety

Naoyoshi Noguchi, Masahisa Nakada^*

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

44 被引用数 (Scopus)

抄録

Asymmetric synthesis of the spirocyclic CD-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety 1a in the presence of a Lewis acid.

本文言語	English
ページ（範囲）	2039-2042
ページ数	4
ジャーナル	Organic Letters
巻	8
号	10
DOI	https://doi.org/10.1021/ol060437x
出版ステータス	Published - 2006 5 11

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

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10.1021/ol060437x

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title = "Synthetic studies on (+)-ophiobolin A: Asymmetric synthesis of the spirocyclic CD-ring moiety",

abstract = "Asymmetric synthesis of the spirocyclic CD-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety 1a in the presence of a Lewis acid.",

author = "Naoyoshi Noguchi and Masahisa Nakada",

year = "2006",

month = may,

day = "11",

doi = "10.1021/ol060437x",

language = "English",

volume = "8",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Synthetic studies on (+)-ophiobolin A

T2 - Asymmetric synthesis of the spirocyclic CD-ring moiety

AU - Noguchi, Naoyoshi

AU - Nakada, Masahisa

PY - 2006/5/11

Y1 - 2006/5/11

N2 - Asymmetric synthesis of the spirocyclic CD-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety 1a in the presence of a Lewis acid.

AB - Asymmetric synthesis of the spirocyclic CD-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety 1a in the presence of a Lewis acid.

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Synthetic studies on (+)-ophiobolin A: Asymmetric synthesis of the spirocyclic CD-ring moiety

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