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^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

49 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2039-2042
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	10
DOIs	https://doi.org/10.1021/ol060437x
Publication status	Published - 2006 May 11

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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",

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doi = "10.1021/ol060437x",

language = "English",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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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

Abstract

ASJC Scopus subject areas

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