title: Synthesis of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester.
abstract: Cascades: An InBr(3)-catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3-oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin-alcohol substrates. In addition, the total synthesis of (±)-moluccanic acid methyl ester was achieved in seven steps by using such a Prins-polyene cyclization as the key step.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore.
authors.forename: Bin
authors.initials: B
authors.lastname: Li
authors.forename: Yin-Chang
authors.initials: YC
authors.lastname: Lai
authors.forename: Yujun
authors.initials: Y
authors.lastname: Zhao
authors.forename: Yiu-Hang
authors.initials: YH
authors.lastname: Wong
authors.forename: Zhi-Liang
authors.initials: ZL
authors.lastname: Shen
authors.forename: Teck-Peng
authors.initials: TP
authors.lastname: Loh
mesh_terms: D003500:Cyclization; D007204:Indium / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis*; D011090:Polyenes / Q000737:chemistry; D011422:Propionates / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009281:Naphthalenes; D011090:Polyenes; D011422:Propionates; D013729:Terpenes; C530781:indium bromide; D007204:Indium