Synthesis and structural determination of the C33–C42 fragment of symbiodinolide

Discovery of benthol A and its challenging stereochemical assignment: opening up a new window for skeletal diversity of super-carbon-chain compounds

“…20 It is the same with 22R in 1A. Most notably, the above assigned 18S and 22R congurations were consistent with the Dd SR sign distribution proposed for the acyclic 1,5-diol systems, as noted by Riguera, [21][22][23][24][25][26][27] viz., a type D syn-1,5-diol for the bis-MTPA esters of the C14-C18 diol moiety and a type B anti-1,5-diol for that of the C18-C22 diol moiety in 1A (Fig. 5).…”

Bioactive secondary metabolites from symbiotic marine dinoflagellates: symbiodinolide and durinskiols

“…The stereochemistry of the C44–C51 tetraol moiety was determined by Kishi's Universal NMR Database method. Furthermore, the degraded fragments 9 , 11 , and 12 , and the C79–C96 model compound 17 have all been synthesized, which clarified their absolute stereochemistries 32–37. To date, the absolute configurations of C17–C40, C69–73, C83–C103, and C3′–C18′ in symbiodinolide ( 1 ) have been confirmed.…”

Marine natural products

“…[Stelletta sp., (Geoje Is., S. Korea)]. 304 Synthesis of the C-33-C-42 fragment established the configurations (36S,40S), 305,306 and also the absolute configuration of the C-1 0 -C-25 0 fragment. 3-Dimethoxy-7-ketocholanic acid, 269 while known, was isolated from a natural source for the first time.…”