Total Synthesis of Cribrostatin IV: Fine-Tuning the Character of an Amide Bond by Remote Control
- 10 March 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (13), 4596-4598
- https://doi.org/10.1021/ja050203t
Abstract
We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a “lynchpin” Mannich cyclization to establish the pentacyclic core (cf. 19 → 20).Keywords
This publication has 29 references indexed in Scilit:
- Synthesis of Saframycins. X. Transformation of (-)-Saframycin A to (-)-Saframycin Mx Type Compound with the Structure Proposed for Saframycin E.CHEMICAL & PHARMACEUTICAL BULLETIN, 1995
- Preparation and use of C2-symmetric bis(phospholanes): production of .alpha.-amino acid derivatives via highly enantioselective hydrogenation reactionsJournal of the American Chemical Society, 1993
- Synthesis of saframycins. VI. The useful transformation of (-)-saframycin a to (-)-saframycin Mx type compound.CHEMICAL & PHARMACEUTICAL BULLETIN, 1991
- Synthesis of saframycins. IV. Selenium oxide oxidation of 4-oxo-hexahydro-1,5-imino-3-benzazocin-7,10-dione; promising method to construct saframycins C and D from saframycin B.CHEMICAL & PHARMACEUTICAL BULLETIN, 1990
- A new synthetic approach to 1-(hydroxymethyl)-8-methoxy-1,2,3,4-tetrahydroisoquinolin-4-oneThe Journal of Organic Chemistry, 1987
- Asymmetric electrophilic substitution on phenols. Enantioselective ortho-hydroxyalkylation mediated by chiral alkoxyaluminum chloridesThe Journal of Organic Chemistry, 1985
- Molecular mechanism of action of 5,6-dihydroxytryptamine. Synthesis and biological evaluation of 4-methyl-, 7-methyl- and 4,7-dimethyl-5,6-dihydroxytryptaminesJournal of Medicinal Chemistry, 1985
- A periodonium trifluoromethanesulfonate. An isolable 10-I-4 organoiodine speciesJournal of the American Chemical Society, 1982
- Synthesis of isoquinolines. VIII. 3,4,11,11a-tetrahydro-1H-benzo[b]quinolizin-2(6H)-onesThe Journal of Organic Chemistry, 1968
- Synthesis of isoquinolines. VII. 4-Hydroxy-1,2,3,4-tetrahydroisoquinolinesThe Journal of Organic Chemistry, 1968