Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Alexander M. Sherwood; Samuel E. Williamson; Stephanie N. Johnson; Anil Yilmaz; Victor W. Day; Thomas E. Prisinzano

doi:10.1021/acs.joc.7b02324

Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Alexander M. Sherwood, Samuel E. Williamson, Stephanie N. Johnson, Anil Yilmaz, Victor W. Day, Thomas E. Prisinzano

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

4 Scopus citations

Abstract

A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.

Original language	English
Pages (from-to)	980-992
Number of pages	13
Journal	Journal of Organic Chemistry
Volume	83
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.7b02324
State	Published - Jan 19 2018

Bibliographical note

Funding Information:
We acknowledge the following for financial support: DA018151 and GM111385 (to T.E.P.); NIH Training Grant GM08545 (to S.E.W.); The Scientific and Technological Research Council of Turkey (TUBITAK) 1059B141400648 Bezmialem Vakif University (to A.Y.); NSF-MRI Grant CHE-0923449 (to V.W.D.). The support for the NMR instrumentation was provided by the NIH Shared Instrumentation Grant no. S10RR024664 and NSF Major Research Instrumentation Grant no. 0320648.

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus subject areas

Organic Chemistry

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title = "Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives",

abstract = "A reliable protocol to synthesize both racemic and chiral (E)-4-iodobut-3-en-1-ols from aldehydes or epoxides, respectively, containing various aromatic and aliphatic substitutions has been established. The utility of these compounds was then demonstrated by providing access to known fungal decanolides as well as novel aromatic macrocycles. The protocol provided a gram-scale route to (-)-aspinolide A and (-)-5-epi-aspinolide A utilizing a catalytic Nozaki-Hiyama-Kishi reaction to close the macrolide in the final step in 65-84% yields.",

author = "Sherwood, {Alexander M.} and Williamson, {Samuel E.} and Johnson, {Stephanie N.} and Anil Yilmaz and Day, {Victor W.} and Prisinzano, {Thomas E.}",

note = "Funding Information: We acknowledge the following for financial support: DA018151 and GM111385 (to T.E.P.); NIH Training Grant GM08545 (to S.E.W.); The Scientific and Technological Research Council of Turkey (TUBITAK) 1059B141400648 Bezmialem Vakif University (to A.Y.); NSF-MRI Grant CHE-0923449 (to V.W.D.). The support for the NMR instrumentation was provided by the NIH Shared Instrumentation Grant no. S10RR024664 and NSF Major Research Instrumentation Grant no. 0320648. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2018",

month = jan,

day = "19",

doi = "10.1021/acs.joc.7b02324",

language = "English",

volume = "83",

pages = "980--992",

number = "2",

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Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives. / Sherwood, Alexander M.; Williamson, Samuel E.; Johnson, Stephanie N. et al.
In: Journal of Organic Chemistry, Vol. 83, No. 2, 19.01.2018, p. 980-992.

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

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T2 - Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

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AU - Williamson, Samuel E.

AU - Johnson, Stephanie N.

AU - Yilmaz, Anil

AU - Day, Victor W.

AU - Prisinzano, Thomas E.

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Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives

Abstract

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