Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C 1-C8 and C15-C21 subunits of (+)-discodermolide

P. Veeraraghavan Ramachandran; Bodhuri Prabhudas; J. Subash Chandra; M. Venkat Ram Reddy

doi:10.1021/jo0492416

Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C ₁-C₈ and C₁₅-C₂₁ subunits of (+)-discodermolide

P. Veeraraghavan Ramachandran
, Bodhuri Prabhudas
, J. Subash Chandra
, M. Venkat Ram Reddy

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

56 Scopus citations

Abstract

Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective α-deoxygenation provides 1,3-trans-β-hydroxy-6- lactones stereoselectively. This protocol has been applied for the synthesis of C₁-C₈ and C₁₅-C₂₁ subunits of (+)-discodermolide.

Original language	English (US)
Pages (from-to)	6294-6304
Number of pages	11
Journal	Journal of Organic Chemistry
Volume	69
Issue number	19
DOIs	https://doi.org/10.1021/jo0492416
State	Published - Sep 17 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo0492416

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title = "Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C 1-C8 and C15-C21 subunits of (+)-discodermolide",

abstract = "Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective α-deoxygenation provides 1,3-trans-β-hydroxy-6- lactones stereoselectively. This protocol has been applied for the synthesis of C1-C8 and C15-C21 subunits of (+)-discodermolide.",

author = "Ramachandran, \{P. Veeraraghavan\} and Bodhuri Prabhudas and Chandra, \{J. Subash\} and Reddy, \{M. Venkat Ram\}",

year = "2004",

month = sep,

day = "17",

doi = "10.1021/jo0492416",

language = "English (US)",

volume = "69",

pages = "6294--6304",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "19",

}

Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C ₁-C₈ and C₁₅-C₂₁ subunits of (+)-discodermolide. / Ramachandran, P. Veeraraghavan; Prabhudas, Bodhuri; Chandra, J. Subash et al.
In: Journal of Organic Chemistry, Vol. 69, No. 19, 17.09.2004, p. 6294-6304.

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

TY - JOUR

T1 - Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones

T2 - A novel protocol for the stereoselective synthesis of C 1-C8 and C15-C21 subunits of (+)-discodermolide

AU - Ramachandran, P. Veeraraghavan

AU - Prabhudas, Bodhuri

AU - Chandra, J. Subash

AU - Reddy, M. Venkat Ram

PY - 2004/9/17

Y1 - 2004/9/17

N2 - Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective α-deoxygenation provides 1,3-trans-β-hydroxy-6- lactones stereoselectively. This protocol has been applied for the synthesis of C1-C8 and C15-C21 subunits of (+)-discodermolide.

AB - Diastereoselective dihydroxylation of dihydropyranones and subsequent regioselective α-deoxygenation provides 1,3-trans-β-hydroxy-6- lactones stereoselectively. This protocol has been applied for the synthesis of C1-C8 and C15-C21 subunits of (+)-discodermolide.

UR - https://www.scopus.com/pages/publications/4644220374

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U2 - 10.1021/jo0492416

DO - 10.1021/jo0492416

M3 - Article

C2 - 15357588

AN - SCOPUS:4644220374

SN - 0022-3263

VL - 69

SP - 6294

EP - 6304

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Diastereoselective dihydroxylation and regioselective deoxygenation of dihydropyranones: A novel protocol for the stereoselective synthesis of C ₁-C₈ and C₁₅-C₂₁ subunits of (+)-discodermolide

Abstract

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