X-ray determination of chondriol; a re-assignment of structure

Marine natural products: metabolites of marine algae and herbivorous marine molluscs

“…Many of these metabolites were reported prior to 1978, and have been extensively reviewed by Fenical. * Recent additions to this group are dictyotriene B (198), dictyone (199), and dictytriol (200), along with pachydictyol A (165), from a Japanese sample of Dictyota dichotoma. 5 2 The hydrocarbons (1 97) and (1 98) are the first hydrocarbons of this series and were not found in all collections of this alga; the authors suggest that the variation in metabolites may be due to 'subtle environmental differences'.…”

Antineoplastic agents. 48. The isolation and structure of aplysistatin

“…These results led to the expectation of those presently reported. (12) This was prepared by the Grignard reaction with pregnenolone followed by acid-catalyzed dehydration. For details and a key to the configurational literature, see W. RRT is the retention time relative to cholesterol in GLC on 1 % of XE-60 on silanized chromosorb W at 235 °C in a 6 ft U-tube.…”

Polyacetylenes of Marine Origin: Chemistry and Bioactivity

“…yamada in 1973, and its structure was wrongly assigned by spectroscopic means as 78 (Figure ) . Successively, the correct structure of chondriol was revised to 79 via X-ray crystallography . Within a study aimed to assess the diversity of halogen-based secondary metabolite biosynthesis in the genus Laurencia, cis - and trans -rhodophytins ( 81 and 82 ) were isolated, along with chondriol ( 79 ) and trans -chondriol ( 80 ) .…”

“…78 Successively, the correct structure of chondriol was revised to 79 via X-ray crystallography. 79 Within a study aimed to assess the diversity of halogen-based secondary metabolite biosynthesis in the genus Laurencia, cis-and trans-rhodophytins (81 and 82) were isolated, along with chondriol (79) and transchondriol (80). 80 Meanwhile, the structure of cis-rhodophytin (81) was revised as the vinyl ether rather than the vinyl peroxide originally proposed.…”