214899-21-5Relevant academic research and scientific papers
Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis
Evans, David A.,Kvaerno, Lisbet,Dunn, Travis B.,Beauchemin, Andre,Raymer, Brian,Mulder, Jason A.,Olhava, Edward J.,Juhl, Martin,Kagechika, Katsuji,Favor, David A.
supporting information; experimental part, p. 16295 - 16309 (2009/05/08)
The synthesis of the marine neurotoxin azaspiracid-1 has been accomplished. The individual fragments were synthesized by catalytic enantioselective processes: A hetero-Diels-Alder reaction to afford the E- and HI-ring fragments, a carbonyl-ene reaction to furnish the CD-ring fragment, and a Mukaiyama aldol reaction to deliver the FG-ring fragment. The subsequent fragment couplings were accomplished by aldol and sulfone anion methodologies. All ketalization events to form the nonacyclic target were accomplished under equilibrating conditions utilizing the imbedded configurations of the molecule to adopt one favored conformation. A final fragment coupling of the anomeric EFGHI-sulfone anion to the ABCD-aldehyde completed the convergent synthesis of (+)-azaspiracid-1.
Total synthesis and structural elucidation of azaspiracid-1. Final assignment and total synthesis of the correct structure of azaspiracid-1
Nicolaou,Koftis, Theocharis V.,Vyskocil, Stepan,Petrovic, Goran,Tang, Wenjun,Frederick, Michael O.,Chen, David Y.-K.,Li, Yiwei,Ling, Taotao,Yamada, Yoichi M. A.
, p. 2859 - 2872 (2007/10/03)
The molecular structure of azaspiracid-1, a neurotoxin isolated from mussels, has been elucidated by total synthesis which also enriched its supplies. The degradatively derived fragments of this marine biotoxin, compounds 5 (EFGHI), 6 (FGHI), and 40 (ABCD
Structural revision and total synthesis of azaspiracid-1, part 2: Definition of the ABCD domain and total synthesis
Nicolaou,Koftis, Theocharis V.,Vyskocil, Stepan,Petrovic, Goran,Ling, Taotao,Yamada, Yoichi M. A.,Tang, Wenjun,Frederick, Michael O.
, p. 4318 - 4324 (2007/10/03)
The chase for the structure of azaspiracid-1 has ended with a revised structure (see picture). The total synthesis of this challenging target has closed another chapter in this intriguing chemical detective story and allowed the assignment of the relative
