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A Unified Strategy for the Syntheses of Angucyclinone Antibiotics: Total Syntheses of Tetrangulol, Kanglemycin M, X‐14881‐E, and Anhydrolandomycinone
Author(s) -
Vanga Devendar Goud,
Kaliappan Krishna P.
Publication year - 2012
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.201200049
Subject(s) - aromatization , chemistry , intramolecular force , diene , enyne metathesis , metathesis , grubbs' catalyst , enyne , total synthesis , combinatorial chemistry , yield (engineering) , stereochemistry , organic chemistry , catalysis , polymerization , natural rubber , polymer , materials science , metallurgy
Abstract A unified strategy for the syntheses of angucyclinone antibiotics was developed utilizing sequential intramolecular enyne metathesis, Diels–Alder/aromatization, photooxygenation, and one‐pot elimination/aromatization reactions. The diversity in this sequence was introduced in the Diels–Alder reaction where a common diene was treated with various appropriately functionalized quinones as the dienophiles to accomplish the total syntheses of tetrangulol, kanglemycin M, X‐14881‐E, and anhydrolandomycinone in moderate to good overall yields. The requisite diene was synthesized in excellent yield from a known enyne through an intramolecular enyne metathesis. The scope of this flexible and divergent strategy can be extended to the syntheses of similar scaffolds and unnatural aromatic angucyclinones.