The Total Synthesis of Psymberin
- 25 May 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (13) , 2597-2600
- https://doi.org/10.1021/ol071068n
Abstract
The total synthesis of a new member of the pederin family of natural products, psymberin 1, was accomplished. Using a recently reported novel and efficient PhI(OAc)2 mediated oxidative entry to 2-(N-acylaminal)-substituted tetrahydropyrans as the key step, this total synthesis was executed in a convergent and efficient manner. The longest linear sequence of this synthesis was 22 steps starting from known 6.Keywords
This publication has 14 references indexed in Scilit:
- Synthesis and Complete Stereochemical Assignment of Psymberin/Irciniastatin AJournal of the American Chemical Society, 2005
- Psymberin, A Potent Sponge-Derived Cytotoxin from Psammocinia Distantly Related to the Pederin FamilyOrganic Letters, 2004
- Antineoplastic Agents. 520. Isolation and Structure of Irciniastatins A and B from the Indo-Pacific Marine Sponge Ircinia ramosaJournal of Medicinal Chemistry, 2004
- The Exceptional Chelating Ability of Dimethylaluminum Chloride and Methylaluminum Dichloride. The Merged Stereochemical Impact of α- and β-Stereocenters in Chelate-Controlled Carbonyl Addition Reactions with Enolsilane and Hydride NucleophilesJournal of the American Chemical Society, 2001
- Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanoneTetrahedron: Asymmetry, 1999
- New catalysts for the asymmetric aldol reaction: chiral boranes prepared from .alpha.,.alpha.-disubstituted glycine arenesulfonamidesJournal of the American Chemical Society, 1991
- Reduction of .beta.-hydroxy ketones with catecholborane. A stereoselective approach to the synthesis of syn-1,3-diolsThe Journal of Organic Chemistry, 1990
- Simple and selective method for aldehydes (RCHO) .fwdarw. (E)-haloalkenes (RCH:CHX) conversion by means of a haloform-chromous chloride systemJournal of the American Chemical Society, 1986
- Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-.beta.-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranesJournal of the American Chemical Society, 1986
- Bicyclo[2.2.1]heptanes as intermediates in the synthesis of steroids. Total synthesis of estroneThe Journal of Organic Chemistry, 1980