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Total Synthesis of Psymberin (Irciniastatin A)

Author:
Yu, Jie, Yang, Mingze, Guo, Yian, Ye, Tao
Source:
Organic letters 2019 v.21 no.10 pp. 3670-3673
ISSN:
1523-7052
Subject:
aldehydes, antineoplastic agents, aromatic compounds, chemical reactions, chemical structure, diastereoselectivity
Abstract:
A convergent, stereocontrolled total synthesis of psymberin, an architecturally complex marine antitumor agent, has been achieved in 27 steps from the known aldehyde 8. Highlights of this synthesis include a novel and efficient transannular Michael addition/lactone reduction sequence to construct the highly substituted 2,6-trans-tetrahydropyran, a diastereoselective IBr-induced iodocarbonate cyclization to introduce the C17 stereogenic center, and a Diels–Alder/aromatization reaction to install the highly substituted aromatic ring.
Agid:
6445846