Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols

Inji Shin; Michael J. Krische

doi:10.1021/acs.orglett.5b02056

Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols

Inji Shin
, Michael J. Krische

Dept. of Fine Chemistry

University of Texas at Austin

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

13 Scopus citations

Abstract

Using stereo- and site-selective C-H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16-27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)-C(32) of the actin-binding macrodiolide swinholide A.

Original language	English
Pages (from-to)	4686-4689
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.5b02056
State	Published - 2 Oct 2015

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title = "Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols",

abstract = "Using stereo- and site-selective C-H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16-27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)-C(32) of the actin-binding macrodiolide swinholide A.",

author = "Inji Shin and Krische, \{Michael J.\}",

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AU - Shin, Inji

AU - Krische, Michael J.

PY - 2015/10/2

Y1 - 2015/10/2

N2 - Using stereo- and site-selective C-H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16-27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)-C(32) of the actin-binding macrodiolide swinholide A.

AB - Using stereo- and site-selective C-H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16-27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)-C(32) of the actin-binding macrodiolide swinholide A.

UR - https://www.scopus.com/pages/publications/84942888553

U2 - 10.1021/acs.orglett.5b02056

DO - 10.1021/acs.orglett.5b02056

M3 - Article

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AN - SCOPUS:84942888553

SN - 1523-7060

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SP - 4686

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JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols

Abstract

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