Toward the Synthesis of Paspaline-Type Indole-Terpenes: Stereoselective Construction of Core Scaffold with Contiguous Asymmetric Quaternary Carbon Centers | Zendy

Ichiro Hayakawa | Zendy; Naochika Matsumaru | Zendy; Akira Sakakura | Zendy

Open Access

Toward the Synthesis of Paspaline-Type Indole-Terpenes: Stereoselective Construction of Core Scaffold with Contiguous Asymmetric Quaternary Carbon Centers

Author(s) -

Ichiro Hayakawa,

Naochika Matsumaru,

Akira Sakakura

Publication year - 2021

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c01193

Subject(s) - chemistry , quaternary carbon , epoxide , chirality (physics) , terpene , stereochemistry , indole test , stereoselectivity , scaffold , core (optical fiber) , enantioselective synthesis , combinatorial chemistry , catalysis , organic chemistry , physics , materials science , quantum mechanics , quark , nambu–jona lasinio model , composite material , medicine , chiral symmetry breaking , biomedical engineering

The core scaffold of paspaline-type indole-terpenes was synthesized by using the House-Meinwald rearrangement as a key step. Rearrangement of the epoxide methyl group in the precursor with methylaluminum bis(4-bromo-2,6-di- er -butylphenoxide) as a Lewis acid proceeded smoothly to construct contiguous asymmetric quaternary carbon centers by a 1,2-chirality transfer.

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