6533b832fe1ef96bd129aeed

RESEARCH PRODUCT

Total Synthesis of epi-Trichosetin.

Till OpatzUlrich KauhlLars Andernach

subject

Natural product010405 organic chemistryStereochemistryOrganic ChemistryTotal synthesis010402 general chemistry01 natural sciences0104 chemical sciencesTrichosetinchemistry.chemical_compoundchemistryYield (chemistry)Intramolecular forceProtecting group

description

The natural 3-decalinoyltetramic acid epi-trichosetin was synthesized in ten steps starting from ( R)-(+)-citronellal using an intramolecular Diels-Alder reaction and a Lacey-Dieckmann cyclization as the key steps. The use of a 2-nitrobenzyl protecting group resulted in an efficient synthetic endgame. The natural product was obtained in 4.1% overall yield.

10.1021/acs.joc.8b02450https://pubmed.ncbi.nlm.nih.gov/30450900