[structure: see text]. The synthesis of a hetero-bis-metallo 1,3-butadiene is reported, and its use as an orthogonal Stille and Suzuki-Miyaura coupling partner is detailed. The tin/boron diene participated successfully in a one-pot, sequential Stille and Suzuki-Miyaura coupling protocol, and its utility was demonstrated in the two-step construction of the pentaene side chain of the Fusarium metabolite lucilactaene.

Hetero-bis-metalated 1,3-butadiene is employed in the lynchpin coupling of synthetic fragments of the side chain of the antitumor agent, lucilactaene. Sequential Stille and Suzuki-Miyaura couplings interpolate this unique boron/tin diene into the pentaene chain. The total synthesis of lucilactaene was accomplished efficiently, in just eight linear steps.

Convergent and efficient syntheses of the microbial natural products gymnoconjugatin A and B are reported and were based on a linchpin coupling strategy using a boron/tin hetero-bis-metallated butadiene system.

No abstract

Polyphenylalkene derivatives Q 0740Tandem Stille/Suzuki-Miyaura Coupling of a Hetero-Bis-Metalated Diene. Rapid, One-Pot Assembly of Polyene Systems. -A new synthesized hetero-bis-metallo 1,3-butadiene is used as a Stille and Suzuki-Miyaura coupling partner. Reactions can be performed consecutively as well as in a one-pot procedure. In dependence of the substituents reaction conditions must be somewhat modified. The present new methodology is also used for the rapid construction of the pentaene side chain of Fusarium metabolite lucilactaene. -(COLEMAN*, R. S.; WALCZAK, M. C.; Org. Lett. 7 (2005) 11, 2289-2291; Dep. Chem., Ohio State Univ., Columbus, OH 43210, USA; Eng.) -S. Adam 42-108

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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.