Synthesis of Pinguisane‐Type Sesquiterpenoids Acutifolone A, Pinguisenol, and Bisacutifolones by a Diels–Alder Dimerization Reaction | Zendy

Shiina Junichi | Zendy; Oikawa Masataka | Zendy; Nakamura Kensuke | Zendy; Obata Rika | Zendy; Nishiyama Shigeru | Zendy

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Synthesis of Pinguisane‐Type Sesquiterpenoids Acutifolone A, Pinguisenol, and Bisacutifolones by a Diels–Alder Dimerization Reaction

Author(s) -

Shiina Junichi,

Oikawa Masataka,

Nakamura Kensuke,

Obata Rika,

Nishiyama Shigeru

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200700522

Subject(s) - chemistry , aldol reaction , stereoselectivity , intermolecular force , diels–alder reaction , total synthesis , monomer , stereochemistry , organic chemistry , molecule , catalysis , polymer

The total synthesis of pinguisane‐type sesquiterpenoids, acutifolone A ( 1 ) and pinguisenol ( 2 ), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels–Alder reaction of these monomeric natural products successfully led to stereoselective dimerization, leading to bisacutifolones A ( 3 ) and B ( 4 ). Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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