The first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one

S. Chandrasekhar; Ch Narsihmulu; S. Shameem Sultana; M. Srinivasa Reddy

doi:10.1016/j.tetlet.2004.10.059

The first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one

S. Chandrasekhar, Ch Narsihmulu, S. Shameem Sultana, M. Srinivasa Reddy

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

38 Scopus citations

Abstract

Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia. Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia.

Original language	English (US)
Pages (from-to)	9299-9301
Number of pages	3
Journal	Tetrahedron Letters
Volume	45
Issue number	50
DOIs	https://doi.org/10.1016/j.tetlet.2004.10.059
State	Published - Dec 6 2004
Externally published	Yes

Bibliographical note

Funding Information:
We C.N., S.S.S., and M.S.R. thank CSIR New Delhi for financial support and S.C. thanks DST, New Delhi for a grant.

Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.

Keywords

Keck asymmetric allylation
Maruoka asymmetric allylation
Ring-closing metathesis

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title = "The first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one",

abstract = "Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia. Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia.",

keywords = "Keck asymmetric allylation, Maruoka asymmetric allylation, Ring-closing metathesis",

author = "S. Chandrasekhar and Ch Narsihmulu and Sultana, {S. Shameem} and {Srinivasa Reddy}, M.",

note = "Funding Information: We C.N., S.S.S., and M.S.R. thank CSIR New Delhi for financial support and S.C. thanks DST, New Delhi for a grant. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.",

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AU - Chandrasekhar, S.

AU - Narsihmulu, Ch

AU - Sultana, S. Shameem

AU - Srinivasa Reddy, M.

N1 - Funding Information: We C.N., S.S.S., and M.S.R. thank CSIR New Delhi for financial support and S.C. thanks DST, New Delhi for a grant. Copyright: Copyright 2012 Elsevier B.V., All rights reserved.

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N2 - Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia. Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia.

AB - Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia. Iterative asymmetric allylations and ring-closing metathesis have been effectively performed for the first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one, a novel α,β-unsaturated-δ-lactone having antifungal activity, isolated from Ravensara crassifolia.

KW - Keck asymmetric allylation

KW - Maruoka asymmetric allylation

KW - Ring-closing metathesis

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The first stereoselective total synthesis of (6S)-5,6-dihydro-6-[(2R)-2- hydroxy-6-phenylhexyl]-2H-pyran-2-one

Abstract

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Keywords

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