250595-70-1Relevant articles and documents
Total synthesis of (+)-halichlorine: An inhibitor of VCAM-1 expression
Trauner, Dirk,Schwarz, Jacob B.,Danishefsky, Samuel J.
, p. 3542 - 3545 (2007/10/03)
The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (a??4) is a key step in the first total synthesis of (+)-halichlorine. A series of protections/deprotections
Studies towards the total synthesis of halichlorine: Asymmetric synthesis of the spiroquinolizidine subunit
Trauner, Dirk,Danishefsky, Samuel J.
, p. 6513 - 6516 (2007/10/03)
The C1-C15 spiroquinolizidine subunit (cf. 2) of the marine natural product halichlorine (1) was prepared in 12 steps starting from the known 'Meyers-lactam' 5. The synthesis involves a B-alkyl-Suzuki coupling followed by a highly stereoselective intramolecular Michael addition and an intramolecular Mannich ring closure.