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Alkynes From Furans: A General Fragmentation Method Applied to the Synthesis of the Proposed Structure of Aglatomin B
Author(s) -
Deng Jiachen,
Wu Jingjing,
Tian Hailong,
Bao Jiajing,
Shi Yong,
Tian Weisheng,
Gui Jinghan
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201712365
Subject(s) - furan , synthon , chemistry , fragmentation (computing) , cycloaddition , combinatorial chemistry , stereochemistry , natural product , singlet oxygen , organic chemistry , computational chemistry , oxygen , computer science , catalysis , operating system
Furans are versatile synthons in organic chemistry. Described is a general method for transforming furans into alkynes by dual C−C double‐bond cleavage. The reaction is proposed to proceed by sequential [4+2] cycloaddition between furan and singlet oxygen and a formal retro‐(3+2) fragmentation of the endoperoxide intermediate. A wide array of furans, including those derived from sapogenins, are amenable to this reaction, thus providing the corresponding alkynoic acids in up to 88 % yields. The synthetic utility was demonstrated by a seven‐step synthesis of the proposed structure of a pregnane natural product, aglatomin B, from a known intermediate.
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