Synthesis of the C1-C13 tetraenoate subunit of the chivosazoles.
Ian Paterson, S B Jennifer Kan, Lisa J Gibson
Index: Org. Lett. 12(16) , 3724-7, (2010)
Full Text: HTML
Abstract
Using a combination of asymmetric vinylogous Mukaiyama aldol and Stille cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and C11 stereocenters of the chivosazoles, terminates in a (Z)-vinyl bromide for the planned cross-coupling to a northern hemisphere fragment.
Related Compounds
Related Articles:
Reactivity in nucleophilic vinylic substitution (S(N)V):S(N)Vπ versus S(N)Vσ mechanistic dichotomy.
2013-09-06
[J. Org. Chem. 78(17) , 8574-84, (2013)]
Asymmetric synthesis of enantioenriched (+)-elaeokanine A.
2006-07-21
[J. Org. Chem. 71(15) , 5674-8, (2006)]
2013-01-21
[Angew. Chem. Int. Ed. Engl. 52(4) , 1266-9, (2013)]
Total synthesis of polycavernoside A, a lethal toxin of the red alga Polycavernosa tsudai.
2005-07-08
[J. Org. Chem. 70(14) , 5449-60, (2005)]
New one-pot synthesis of (E)-beta-aryl vinyl halides from styrenes.
2009-08-06
[Org. Lett. 11(15) , 3390-3, (2009)]