Synthesis of the bis-spiroacetal C25-C40 moiety of the antimitotic agent spirastrellolide B using a bis-dithiane deprotection/spiroacetalisation sequence.
Use of a bis-dithiane deprotection-tandem bis-spiroacetalisation sequence was key to the successful synthesis of the [5,6,6]-bis-spiroacetal of the antimitotic agent spirastrellolide B, achieved in a highly convergent fashion involving successive dithiane alkylations.
Chen
Jack Li-Yang
JL
Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland, New Zealand.
Brimble
Margaret A
MA
D000478:Alkylation; D050256:Antimitotic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D054648:Protein Phosphatase 2 / Q000037:antagonists & inhibitors / Q000378:metabolism; D011807:Quinolizines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry*
D050256:Antimitotic Agents; D018942:Macrolides; D011807:Quinolizines; D013141:Spiro Compounds; D013457:Sulfur Compounds; C438055:dithiane; C519027:spirastrellolide B; D054648:Protein Phosphatase 2