Phoracantha synonyma

Products from silicon-modified acyloin condensations have also been used successfully in syntheses of macrocylic lactones. For example, decan-9-olide (a defensive secretion of Phoracantha synonyma) has been synthesized from... 

The ten-membered lactone (R)-(-)-phoracantholide I [(-)-VII/126] [66] was first isolated from the metasternal gland of the eucarypt longicorn Phoracantha synonyma Newman [67]. It is part of the beetle s defensive secretion. Several times in the past this compound has been synthesized several times using ring forming [68] [69] [70] [71] [72] [73], as well as ring enlargement reactions [3] [74] [75] [76] [77] [78] [79] [80] [81] [82],... 

Phoracantholide I (Fig. 27, 154) is a defense secretion of the eucarypt longi-com, Phoracantha synonyma, and it is a 10-membered ring macrolide [181]. 

Moore, B. R, and Brown, W. V. (1976). The chemistry of the metastemal gland secretion of the eucalypt longicom Phoracantha synonyma (Coleoptera Cerambycidae). Aust. J. Chem. 29, 1365-1374. 

Baldwin et al. used a radical-mediated ring expansion of 3-stannylcyclohexanones to provide efficient routes to cis-and trans-cyclononenones. Thus, bromo ketone 109 underwent a radical reaction to generate cyclopentyl aUcoxy radical 110. Fragmentation and elimination of a stannyl radical led to cyclononenone 111, which was further elaborated to rac-phoracantholide I (Scheme 25.52), originally isolated from the metastemal secretion of the eucalypt lon-gicom Phoracantha synonyma. 

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