Construction of the Tricyclic Furanochroman Skeleton of Phomactin A via the Prins/Conia-Ene Cascade Cyclization Approach

Shuangping Huang; Guangyan Du; Chi Sing Lee

doi:10.1021/jo200644t

Construction of the Tricyclic Furanochroman Skeleton of Phomactin A via the Prins/Conia-Ene Cascade Cyclization Approach

Shuangping Huang
, Guangyan Du
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

45 Citations (Scopus)

Abstract

A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf) ₃ in CH ₃CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/ dealkoxycarbonylation protocol under very mild conditions with 52% yield in three steps.

Original language	English
Pages (from-to)	6534-6541
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	76
Issue number	16
Early online date	8 Jul 2011
DOIs	https://doi.org/10.1021/jo200644t
Publication status	Published - 19 Aug 2011

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title = "Construction of the Tricyclic Furanochroman Skeleton of Phomactin A via the Prins/Conia-Ene Cascade Cyclization Approach",

abstract = "A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf) 3 in CH 3CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66\% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/ dealkoxycarbonylation protocol under very mild conditions with 52\% yield in three steps.",

author = "Shuangping Huang and Guangyan Du and Lee, \{Chi Sing\}",

note = "Financial support for this research project from the National Natural Science Foundation of China (Grant No.: 20972004) and Peking University Shenzhen Graduate School is gratefully acknowledged. A special acknowledgment is made to the Hong Kong Polytechnic University, which is funded by the University Grants Committee of Hong Kong Special Equipment Grant, for the 500 and 600 MHz NMR spectrometers. Publisher Copyright: {\textcopyright} 2011 American Chemical Society",

year = "2011",

month = aug,

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doi = "10.1021/jo200644t",

language = "English",

volume = "76",

pages = "6534--6541",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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AU - Huang, Shuangping

AU - Du, Guangyan

AU - Lee, Chi Sing

N1 - Financial support for this research project from the National Natural Science Foundation of China (Grant No.: 20972004) and Peking University Shenzhen Graduate School is gratefully acknowledged. A special acknowledgment is made to the Hong Kong Polytechnic University, which is funded by the University Grants Committee of Hong Kong Special Equipment Grant, for the 500 and 600 MHz NMR spectrometers. Publisher Copyright: © 2011 American Chemical Society

PY - 2011/8/19

Y1 - 2011/8/19

N2 - A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf) 3 in CH 3CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/ dealkoxycarbonylation protocol under very mild conditions with 52% yield in three steps.

AB - A substrate-controlled asymmetric Prins/Conia-ene cascade cyclization has been developed with In(OTf) 3 in CH 3CN from 0 to 70 °C. These conditions afforded very good yields of the 1-oxadecalin product in one pot and effectively suppressed the racemization of the 1-oxadecalin product with almost no enantiomeric excess (ee) loss. This cascade cyclization has been successfully employed for the construction of the highly functionalized 1-oxadecalin unit of phomactin A with an acyclic β-keto ester and an alkynal as the substrates via a one-pot operation (66% yield, single diastereomer). The 1-oxadecalin moiety has been readily converted to the tricyclic furanochroman skeleton of phomactin A via the epoxidation/ dealkoxycarbonylation protocol under very mild conditions with 52% yield in three steps.

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VL - 76

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 16

ER -

Construction of the Tricyclic Furanochroman Skeleton of Phomactin A via the Prins/Conia-Ene Cascade Cyclization Approach

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