Synthesis of the C3-C18 fragment of amphidinolides G and H.
A synthesis of an amphidinolides G and H C3-C18 subunits is reported. The C10-C18 segment 4 was prepared by a Negishi cross-coupling, whereas the synthesis of the C3-C9 fragment 5 employed an asymmetric cyanosilylation as the key step. The two segments were coupled by lithiation of iodide 4 and trapping of the anion with amide 5. The allylic epoxide moiety could be synthesized from the protected anti- mesylate 22.
Petri
Andreas F
AF
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8103, USA.
Schneekloth
John S
JS
Mandal
Amit K
AK
Crews
Craig M
CM
D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000097442:Amphidinolides
D018942:Macrolides; C414663:amphidinolide G; D000097442:Amphidinolides; C414664:amphidinolide H