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

8 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

Publisher Copyright:
© 2017 American Chemical Society.

Funding

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.

Funders	Funder number
NSF-MRI	CHE-0923449, S10RR024664
TUBITAK	1059B141400648
U.S. Department of Energy Chinese Academy of Sciences Guangzhou Municipal Science and Technology Project Oak Ridge National Laboratory Extreme Science and Engineering Discovery Environment National Science Foundation National Energy Research Scientific Computing Center National Natural Science Foundation of China	0320648
U.S. Department of Energy Chinese Academy of Sciences Guangzhou Municipal Science and Technology Project Oak Ridge National Laboratory Extreme Science and Engineering Discovery Environment National Science Foundation National Energy Research Scientific Computing Center National Natural Science Foundation of China
National Institutes of Health (NIH)	GM08545
National Institutes of Health (NIH)
National Institute of General Medical Sciences	R24GM111385
National Institute of General Medical Sciences
Türkiye Bilimsel ve Teknolojik Araştirma Kurumu
Bezmialem Vakıf Üniversitesi

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.7b02324

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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 = "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

TY - JOUR

T1 - Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols

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

AU - Sherwood, Alexander M.

AU - Williamson, Samuel E.

AU - Johnson, Stephanie N.

AU - Yilmaz, Anil

AU - Day, Victor W.

AU - Prisinzano, Thomas E.

PY - 2018/1/19

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AB - 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.

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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

Bibliographical note

Funding

ASJC Scopus subject areas

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