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
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.
