“…The aim of this review is to describe all macrolactonization reactions involving the activation of one or the other extremity of the seco-acid. This topic has been previously covered in part by several reviews at the end of the 1970s and in the mid 1990s; however, to the best of our knowledge no recent coverage has appeared in the literature. − The literature is surveyed until mid-2004. 1 Some representative examples of natural macrocyclic lactones.…”
Section: Introductionmentioning
confidence: 99%
“…This topic has been previously covered in part by several reviews at the end of the 1970s and in the mid 1990s; however, to the best of our knowledge no recent coverage has appeared in the literature. [14][15][16][17][18][19][20] The literature is surveyed until mid-2004.…”
“…The aim of this review is to describe all macrolactonization reactions involving the activation of one or the other extremity of the seco-acid. This topic has been previously covered in part by several reviews at the end of the 1970s and in the mid 1990s; however, to the best of our knowledge no recent coverage has appeared in the literature. − The literature is surveyed until mid-2004. 1 Some representative examples of natural macrocyclic lactones.…”
Section: Introductionmentioning
confidence: 99%
“…This topic has been previously covered in part by several reviews at the end of the 1970s and in the mid 1990s; however, to the best of our knowledge no recent coverage has appeared in the literature. [14][15][16][17][18][19][20] The literature is surveyed until mid-2004.…”
“…To further illustrate the utility of this method, the one-pot protocol was applied for the total synthesis of the (±)-Recifeiolide, a naturally occurring macrolide (Scheme ). This 12-membered lactone has been isolated as a metabolite of a fungus Cephalosporium recifei .…”
mentioning
confidence: 99%
“…From commercially available reagents, the synthesis involves five steps with an overall yield of 35%. This is one of the most concise total synthesis of the (±)-Recifeiolide …”
The first Ni-catalyzed Suzuki-Miyaura coupling of alkyl halides with alkenyl-(9-BBN) reagents is reported. Both primary and secondary alkyl halides including alkyl chlorides can be coupled. The coupling method can be combined with hydroboration of terminal alkynes, allowing the expedited synthesis of functionalized alkyl alkenes from readily available alkynes with complete (E)-selectivity in one pot. The method was applied to the total synthesis of (±)-Recifeiolide, a natural macrolide.
“…Stereocontrolled synthesis of macrolide antibiotics is one of the most attractive areas in current synthetic organic chemistry, and various new synthetic methodologies have been developed en route to the synthesis of such complex molecules . The methymycin family of antibiotics comprises three 12-membered macrolides isolated from Streptomyces species methymycin, neomethymycin, and 10-deoxymethymycin that display antibiotic activity against Gram-positive bacteria.…”
A highly stereoselective and convergent formal total synthesis of (+)-methynolide is described. The salient features of this synthesis have been the construction of the C1-C7 and C8-C11fragments via a desymmetrization approach, Sharpless asymmetric epoxidation of an allyl alcohol, respectively, and linkage of both the fragments by Nozaki-Hiyama-Kishi reaction.
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