Studies toward the total synthesis of garsubellin A: a concise synthesis of the 18-epi-tricyclic core.
[reaction: see text] During studies directed toward the total synthesis of garsubellin A, a concise stereocontrolled synthesis of the 18-epi-tricyclic compound 3 was achieved. Key steps were a one-pot stereoselective construction of the bicyclic lactone 23 followed by a formal migration to the bicyclo[3.3.1]nonane-1,3,5-trione and an intramolecular Wacker-type tetrahydrofuran ring formation.
Usuda
Hiroyuki
H
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kanai
Motomu
M
Shibasaki
Masakatsu
M
D002795:Choline O-Acetyltransferase / Q000187:drug effects; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
D006575:Heterocyclic Compounds, 3-Ring; D007783:Lactones; D013729:Terpenes; C106690:garsubellin A; D002795:Choline O-Acetyltransferase