Formal total synthesis of salicylihalamides A and B.
An efficient synthesis of the macrolactone 3 of the salicylihalamides in 10 linear steps from alkene 6 is described. The key steps involved a Stille coupling between the chiral stannane 5 and benzyl bromide 4, which produced alkene 15 in good yield, and subsequent base-induced macrolactonization then gave compound 3. Macrolactone 3 was then converted into the known salicylihalamide A intermediate 18 in a three-step sequence. Compound 3 was also converted into another known salicylihalamide A and B intermediate 23 in a five-step sequence.
Holloway
Georgina A
GA
School of Chemistry, The University of Melbourne, Victoria 3010, Australia.
Hügel
Helmut M
HM
Rizzacasa
Mark A
MA
D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry
D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D007783:Lactones; C410986:salicylihalamide A