A Total Synthesis of the Racemic Sesquiterpene Parvifoline
摘要:
A total synthesis of the sesquiterpene (+/-)-parvifoline 1 from the symmetrical naphthalene 4 is reported. The key step of the synthesis was a Stork-Landesman two-carbon ring expansion of beta-tetralone 5, which affords 9a with the complete framework of the target. Although many reactions are involved in the sequence, the whole synthesis can be executed in only five synthetic operations and in approximate to 18% overall yield.
Syntheses of 5-, 7-, and 8-methoxy-3-methyl-2-tetralones
作者:Anette M. Johansson、Charlotta Mellin、Uli Hacksell
DOI:10.1021/jo00376a038
日期:1986.12
REBEK, J. ,, JR.;MARSHALL, L.;WOLAK, R.;PARRIS, K.;KILLORAN, M.;ASKEW, B.+, J. AMER. CHEM. SOC., 1985, 107, N 25, 7476-7481
作者:REBEK, J. ,, JR.、MARSHALL, L.、WOLAK, R.、PARRIS, K.、KILLORAN, M.、ASKEW, B.+
DOI:——
日期:——
JOHANSSON A. M.; MELLIN CH.; HACKSELL U., J. ORG. CHEM., 51,(1986) N 26, 5252-5258
作者:JOHANSSON A. M.、 MELLIN CH.、 HACKSELL U.
DOI:——
日期:——
Convergent functional groups: synthetic and structural studies
作者:Julius Rebek、Luann Marshall、Raymond Wolak、Kevin Parris、Mary Killoran、Ben Askew、David Nemeth、N. Islam
DOI:10.1021/ja00311a042
日期:1985.12
A Total Synthesis of the Racemic Sesquiterpene Parvifoline
作者:Adrián Covarrubias-Zúñiga、Fernando Cantú、Luis A. Maldonado
DOI:10.1021/jo972092p
日期:1998.5.1
A total synthesis of the sesquiterpene (+/-)-parvifoline 1 from the symmetrical naphthalene 4 is reported. The key step of the synthesis was a Stork-Landesman two-carbon ring expansion of beta-tetralone 5, which affords 9a with the complete framework of the target. Although many reactions are involved in the sequence, the whole synthesis can be executed in only five synthetic operations and in approximate to 18% overall yield.