Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products

Hong Shuang Wang; Hui Jing Li; Xiang Nan; Yuan Yuan Luo; Yan Chao Wu

doi:10.1021/acs.joc.7b02413

Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products

Hong Shuang Wang
, Hui Jing Li^*
, Xiang Nan
, Yuan Yuan Luo
, Yan Chao Wu

^*Corresponding author for this work

School of Marine Science and Technology, Harbin Institute of Technology Weihai
Peking University

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

26 Scopus citations

Abstract

An enantiospecific semisynthesis of puupehedione was achieved from sclareolide in only 7 steps with an overall yield of 25%. The key drimanal trimethoxystyrene skeleton was constructed by the palladium-catalyzed cross-coupling reaction of an aryl iodine and a drimanal hydrazone. An in situ CAN-oxidation/intramolecular oxa-Stork-Danheiser transposition tandem reaction was used as a powerful tool to install concurrently the C and D rings of puupehedione in a one-pot fashion. Its applicability was also showcased by the semisynthesis of puupehenone and puupehenol.

Original language	English
Pages (from-to)	12914-12919
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	82
Issue number	23
DOIs	https://doi.org/10.1021/acs.joc.7b02413
State	Published - 1 Dec 2017
Externally published	Yes

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This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

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10.1021/acs.joc.7b02413

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title = "Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products",

abstract = "An enantiospecific semisynthesis of puupehedione was achieved from sclareolide in only 7 steps with an overall yield of 25\%. The key drimanal trimethoxystyrene skeleton was constructed by the palladium-catalyzed cross-coupling reaction of an aryl iodine and a drimanal hydrazone. An in situ CAN-oxidation/intramolecular oxa-Stork-Danheiser transposition tandem reaction was used as a powerful tool to install concurrently the C and D rings of puupehedione in a one-pot fashion. Its applicability was also showcased by the semisynthesis of puupehenone and puupehenol.",

author = "Wang, \{Hong Shuang\} and Li, \{Hui Jing\} and Xiang Nan and Luo, \{Yuan Yuan\} and Wu, \{Yan Chao\}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.joc.7b02413",

language = "英语",

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T1 - Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products

AU - Wang, Hong Shuang

AU - Li, Hui Jing

AU - Nan, Xiang

AU - Luo, Yuan Yuan

AU - Wu, Yan Chao

PY - 2017/12/1

Y1 - 2017/12/1

N2 - An enantiospecific semisynthesis of puupehedione was achieved from sclareolide in only 7 steps with an overall yield of 25%. The key drimanal trimethoxystyrene skeleton was constructed by the palladium-catalyzed cross-coupling reaction of an aryl iodine and a drimanal hydrazone. An in situ CAN-oxidation/intramolecular oxa-Stork-Danheiser transposition tandem reaction was used as a powerful tool to install concurrently the C and D rings of puupehedione in a one-pot fashion. Its applicability was also showcased by the semisynthesis of puupehenone and puupehenol.

AB - An enantiospecific semisynthesis of puupehedione was achieved from sclareolide in only 7 steps with an overall yield of 25%. The key drimanal trimethoxystyrene skeleton was constructed by the palladium-catalyzed cross-coupling reaction of an aryl iodine and a drimanal hydrazone. An in situ CAN-oxidation/intramolecular oxa-Stork-Danheiser transposition tandem reaction was used as a powerful tool to install concurrently the C and D rings of puupehedione in a one-pot fashion. Its applicability was also showcased by the semisynthesis of puupehenone and puupehenol.

UR - https://www.scopus.com/pages/publications/85036622500

U2 - 10.1021/acs.joc.7b02413

DO - 10.1021/acs.joc.7b02413

M3 - 文章

C2 - 29083172

AN - SCOPUS:85036622500

SN - 0022-3263

VL - 82

SP - 12914

EP - 12919

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

Enantiospecific Semisynthesis of Puupehedione-Type Marine Natural Products

Abstract

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