Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry

Valerie A. Keller; Ikyon Kim; Steven D. Burke

doi:10.1021/ol0473400

Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry

Valerie A. Keller, Ikyon Kim, Steven D. Burke

Department of Pharmacy

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

22 Citations (Scopus)

Abstract

(Chemical Equation Presented) The C22-C34 portion (2) of halichondrin B was synthesized from meso-symmetric bis-silyl protected cyclopentenediol (7) in 20 steps and 7% overall yield. This was accomplished through a two-directional synthesis/terminus differentiation strategy that proceeded via achiral, mesosymmetric intermediates for eight steps and employed a Pd(0)-mediated asymmetric double cycloetherification to establish both tetrahydropyran rings.

Original language	English
Pages (from-to)	737-740
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	4
DOIs	https://doi.org/10.1021/ol0473400
Publication status	Published - 2005 Feb 17

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0473400

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abstract = "(Chemical Equation Presented) The C22-C34 portion (2) of halichondrin B was synthesized from meso-symmetric bis-silyl protected cyclopentenediol (7) in 20 steps and 7% overall yield. This was accomplished through a two-directional synthesis/terminus differentiation strategy that proceeded via achiral, mesosymmetric intermediates for eight steps and employed a Pd(0)-mediated asymmetric double cycloetherification to establish both tetrahydropyran rings.",

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AU - Kim, Ikyon

AU - Burke, Steven D.

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N2 - (Chemical Equation Presented) The C22-C34 portion (2) of halichondrin B was synthesized from meso-symmetric bis-silyl protected cyclopentenediol (7) in 20 steps and 7% overall yield. This was accomplished through a two-directional synthesis/terminus differentiation strategy that proceeded via achiral, mesosymmetric intermediates for eight steps and employed a Pd(0)-mediated asymmetric double cycloetherification to establish both tetrahydropyran rings.

AB - (Chemical Equation Presented) The C22-C34 portion (2) of halichondrin B was synthesized from meso-symmetric bis-silyl protected cyclopentenediol (7) in 20 steps and 7% overall yield. This was accomplished through a two-directional synthesis/terminus differentiation strategy that proceeded via achiral, mesosymmetric intermediates for eight steps and employed a Pd(0)-mediated asymmetric double cycloetherification to establish both tetrahydropyran rings.

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Synthetic efforts toward the C22-C36 subunit of halichondrin B utilizing local and imposed symmetry

Abstract

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