246245-91-0Relevant academic research and scientific papers
Synthesis of the substituted spiro segment of halichlorine - Use of radical cyclization and stereospecific cuprate addition to an α,β-unsaturated lactam
Yu, Maolin,Clive, Derrick L. J.,Yeh, Vince S.C.,Kang, Shunzhen,Wang, Jian
, p. 2879 - 2881 (2004)
Radical cyclization (26a,b→27a,b+28) and cuprate addition (28→31) were used as key steps to construct the spiro core 4 of halichlorine.
Total synthesis of the marine alkaloid halichlorine: Development and use of a general route to chiral piperidines
Liu, Dazhan,Acharya, Hukum P.,Yu, Maolin,Wang, Jian,Yeh, Vince S. C.,Kang, Shunzhen,Chiruta, Chandramouli,Jachak, Santosh M.,Clive, Derrick L. J.
supporting information; experimental part, p. 7417 - 7428 (2010/02/17)
(Chemical Equation Presented) The total synthesis of the marine alkaloid halichlorine is described, based on an approach that involves constructing the fully substituted asymmetric center at an early stage. The five-membered ring is formed by 5-exo-trig r
A chiral base desymmetrisation - Ring-closing metathesis route to chiral azaspirocycles: Synthesis of core structures related to pinnaic acid and halichlorine
Huxford, Timothy,Simpkins, Nigel S.
, p. 2295 - 2298 (2007/10/03)
A range of highly functionalised chiral azaspirocycles was synthesised, starting from a piperidine diester that is available in 90% ee from a chiral base desymmetrisation. The approach depends upon the use of Grignard addition reactions or a Claisen rearr
Highly enantioselective synthesis of substituted piperidines using the chiral lithium amide base approach
Goldspink, Nicholas J.,Simpkins, Nigel S.,Beckmann, Marion
, p. 1292 - 1294 (2007/10/03)
The symmetry-breaking enolisation reaction of a meso-piperidine diester using a chiral bis-lithium amide base allows access to alkylated derivatives in highly diastereo- and enantioselective fashion (> 98% ee).
