Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.
Under the conditions of C-C bond forming transfer hydrogenation, 1,3-propanediol 1 engages in double asymmetric carbonyl allylation to furnish the C(2)-symmetric diol 2. Double ozonolysis of 2 followed by TBS protection delivers aldehyde 3, which is subject to catalyst directed carbonyl reverse prenylation via transfer hydrogenation to deliver neopentyl alcohol 4 and, ultimately, the bryostatin A-ring 7. Through use of two consecutive C-C bond forming transfer hydrogenations, the Evans' bryostatin A-ring 7 is prepared in less than half the manipulations previously reported.
Lu
Yu
Y
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Krische
Michael J
MJ
D000818:Animals; D054713:Bryostatins / Q000138:chemical synthesis* / Q000737:chemistry; D002013:Bryozoa / Q000737:chemistry; D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D011409:Propylene Glycols / Q000737:chemistry*
D054713:Bryostatins; D011409:Propylene Glycols; C041787:1,3-propanediol