Official websites use .gov
A
.gov website belongs to an official
government organization in the United States.
Secure .gov websites use HTTPS
A lock (
) or https:// means you've safely
connected to the .gov website. Share sensitive
information only on official, secure websites.
Syntheses of (+)-deoxocassine ((2S,3S,6R)-190a, R = C12H25) and (+)-spectaline ((2S,3S,6R)-190b, R = C12H24C(O)Me). Reagents and conditions: a) HC≡CCOOEt, LiHMDS, THF, −78 °C, 2 h; b) TfOTBDMS, 2,6-lutidine, CH2Cl2, 0 °C, 10 min.; c) MeONHMe, iPrCl, THF, −10 °C, 1 h; d) C12H25MgBr, THF, 0 °C to rt, 1 h; e) HC≡C(CH2)10C(OCH2)2CH3, LiHMDS, THF, −78 °C, 1 h; f) H2, 20% Pd(OH)2/C, MeOH, rt, 12 h; g) 1 M HCl, THF, rt, 24 h.
