Total
Synthesis of Verruculogen and Fumitremorgin
A Enabled by Ligand-Controlled C–H Borylation
Yu Feng
Dane Holte
Jochen Zoller
Shigenobu Umemiya
Leah R. Simke
Phil S. Baran
10.1021/jacs.5b07154.s004
https://acs.figshare.com/articles/dataset/Total_Synthesis_of_Verruculogen_and_Fumitremorgin_A_Enabled_by_Ligand_Controlled_C_H_Borylation/2139982
Verruculogen and fumitremorgin
A are bioactive alkaloids
that contain a unique eight-membered endoperoxide. Although
related natural products such as fumitremorgins B and C have
been previously synthesized, we report the first synthesis of the
more complex, endoperoxide-containing members of this family.
A concise route to verruculogen and fumitremorgin A relied
not only on a hydroperoxide/indole hemiaminal cyclization, but also
on the ability to access the seemingly simple starting material, 6-methoxytryptophan.
An iridium-catalyzed C–H borylation/Chan–Lam procedure
guided by an <i>N</i>-TIPS group enabled the conversion
of a tryptophan derivative into a 6-methoxytryptophan derivative,
proving to be a general way to functionalize the C6 position of an <i>N</i>,C3-disubstituted indole for the synthesis of indole-containing
natural products and pharmaceuticals.
2015-08-19 00:00:00
bioactive alkaloids
C 6 position
methoxy
synthesis
endo
fumitre
Total Synthesis