PDF herunterladen
Synfacts 2017; 13(02): 0117
DOI: 10.1055/s-0036-1589874
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of a Ladderane Phospholipid

Rezensent(en):
Erick M. Carreira
,
Leonardo J. Nannini
Mercer JA. M, Cohen CM, Shuken SR, Wagner AM, Smith MW, Moss III FR, Smith MD, Vahala R, Gonzalez-Martinez A, * Boxer SG, * Burns NZ. * Stanford University, USA and Aalto University, Finland
Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid.

J. Am. Chem. Soc. 2016;
138: 15845-15848
CrossrefSuche in Google Scholar
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
18. Januar 2017 (online)

 
 als PDF herunterladen Lizenzen und Reprints

Key words

[2+2] cycloaddition - [5]-ladderanoic acid - [3]-ladderanol - ladderane phospholipids - Ramberg–Bäcklund reaction

Significance

Gonzalez-Martinez, Boxer, Burns and co-workers report an impressive total synthesis of a ladderane phospholipid based on strategic [2+2] cycloadditions of bicyclohexene B, which is obtained by means of a Ramberg–Bäcklund ring contraction of sulfoxide A.


#

Comment

Bicyclohexene B irradiated in the presence of CuOTf gave pentacycle F, which was subjected to an oxidative chlorination–elimination sequence to give cyclobutene I. Enantioselective hydroboration and four further steps yielded [5]-ladderanoic acid.


#
#


   Lizenzen und Reprints