Studies on the synthesis of apoptolidin A. 1. Synthesis of the C(1)-C(11) fragment.
A synthesis of the C(1)-C(11) fragment of apoptolidin A has been accomplished by a convergent route involving the stereoselective glycosidation of 9 and the Suzuki cross-coupling reaction of bromodienoate 7 and the vinylborane generated via chemoselective hydroboration of diyne 6 with diisopinocampheylborane.
Handa
Masaki
M
Department of Chemistry, Scripps-Florida, Jupiter, Florida 33458, USA.
Scheidt
Karl A
KA
Bossart
Martin
M
Zheng
Nan
N
Roush
William R
WR
D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013865:Thioglycosides / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D018942:Macrolides; D020005:Propanols; D011753:Pyrones; D013865:Thioglycosides; C506738:apoptolidin A; D002244:Carbon; C028255:propargyl alcohol