title: Synthesis of the bis-spiroacetal core of the antimitotic agent spirastrellolide B.
abstract: The spirastrellolides are a family of potent antimitotic agents isolated from the marine sponge  Spirastrella coccinea . Synthetic studies toward the DEF bis-spiroacetal core of spirastrellolide B are reported. A modular approach was pursued by the use of two dithiane disconnections to enable a highly convergent synthesis. The ease of lithiation and nucleophilicity of these 2-substituted-1,3-dithianes were investigated during the course of the synthesis, and the alkylations were found to proceed most efficiently at elevated temperatures. Formation of the [5,6,6]-bis-spiroacetal ring system was achieved via a double dithiane deprotection/spiroacetalization strategy.
authors: School of Chemical Sciences, University of Auckland, Auckland, New Zealand.
authors: Jack Li-Yang
authors: JL
authors: Chen
authors: Margaret A
authors: MA
authors: Brimble
mesh_terms: D000478:Alkylation; D050256:Antimitotic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D050256:Antimitotic Agents; D001688:Biological Products; D018942:Macrolides; D011807:Quinolizines; D013141:Spiro Compounds; D013457:Sulfur Compounds; C438055:dithiane; C519027:spirastrellolide B