Open AccessTotal Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G
Author(s) -
Lingbowei Hu,
Viresh H. Rawal
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c05762
Subject(s) - chemistry , total synthesis , cycloaddition , ketone , natural product , yield (engineering) , diene , enone , convergent synthesis , chemical synthesis , stereochemistry , indole test , indole alkaloid , combinatorial chemistry , organic chemistry , catalysis , biochemistry , materials science , natural rubber , metallurgy , in vitro
Reported herein is the total synthesis of (+)-ambiguine G, the first member of the chlorinated pentacyclic ambiguines to yield to chemical synthesis. The synthesis is accomplished through a convergent strategy that proceeds in 10 steps from ( S )-carvone oxide. Pivotal to the concise route is the successful realization of a [4+3] cycloaddition that conjoins two easily synthesized components of the carbon framework of the natural product. Also featured in the synthesis is the efficient, diastereoselective construction of a key vinylated chloro ketone and the unprecedented, one-pot reduction-elimination-oxidation sequence that transforms an enone to an advanced hydroxylated-diene intermediate.