Resorcylic macrolides

Aigialomycins A-E 20-24, new 14-membered resorcylic macrolides, were isolated from the mangrove fungus Aigialus parvus BCC 5311/ ... 

After masking of the alkyne function by a dicobalthexacarbonyl complex, RCM was used to cyclize the diene 573 (Scheme 9.15). Then, decomplexation enabled a Diels-Alder reaction with the disiloxydiene 575, ensued by elimination of isobutylene. Two hydroxy groups of the resorcylic macrolide (576) obtained were protected and the TBS-ether was cleaved. Thus, dehydration with concluding deprotection of all alcohol functions furnished aigialomycin D (482), in an overall yield of 8%. 

Kalivretenos K, Stille JK, Hegedus LS (1991) Synthesis of p-Resorcylic Macrolides via Organopalladium Chemistry. Application to the Total Synthesis of (S)-Zearalenone. J Org... 

Ley SV, Burckhardt S (2000) The Use of Tt-Allyltricarbonyliron Lactone Complexes in the Synthesis of the Resorcylic Macrolides a- and p-Zearalenol. J Chem Soc Perkin Trans 1 3028... 

In 2004, trans- and cw-resorcylide were totally synthesized, and palladium-catalyzed carbonylative Stille coupling was applied for the preparation of the intermediate (Scheme 10.27) [112]. Trans- and cii-resorcylides are both natural macrocyclic plant growth inhibitors, isolated independently from different Peni-cillium species. Together with zearalenone, lasiodiplodin, and the important antitumor agent radicicol, they constimte an important class of bioactive resorcylic macrolides. 

Isaka, M., Suyarnsestakorn, C., Tanticharoen, M., Kongsaeree, P., and Thebtaranonlh, Y. (2002) Aigialomycins A-E, new resorcylic macrolides from the marine mangrove fungus Aigialus parvus. J. Org. Chem., 67,1561-1566. 

The resorcylic acid lactones (RALs) are a family of benzannulated macrolides, which are produced by a variety of fungi and show versatile biological activities (6). According to their name, they consist structurally of a partially substituted p-resorcylic acid scaffold, which is linked to a 12- or 14-membered macrolactone moiety. Selected members of this group are shown in Fig. 9.1. 

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