Didemniserinolipids A−C, Unprecedented Serinolipids from the Tunicate Didemnum sp.

A formal synthesis of (+)-didemniserinolipid B employing a Pd-mediated 6-endo selective alkynediol cycloisomerization

“…Didemniserinolipids A-C were isolated from the methanol extract of marine tunicate Didemnum sp., by González et al in 1999 as the first examples of serinolipids with a unique 6,8-dioxabicyclo[3,2,1]octane core. 7 Subsequent to the isolation of cyclodidemniserinol trisulfate, a related serinolipid with promising HIV-integrase inhibition by Faulkner and co-workers, 8 these serinolipids have attracted considerable synthetic interest.…”

“…7 Subsequent to the isolation of cyclodidemniserinol trisulfate, a related serinolipid with promising HIV-integrase inhibition by Faulkner and co-workers, 8 these serinolipids have attracted considerable synthetic interest. 9,10 The assigned constitution and the relative stereochemistry of the didemniserinolipid B has been cross-checked by chemical Fig.…”

Microwave-Assisted Natural Product Chemistry

“…S.V. Ley et al [16] developed a multistep sequence starting from D-(or L-) serinol and a known butanediacetal (BDA)-protected chiral building block [17] to prove by synthesis the absolute and relative stereochemistry of (+)-Didemniserinolipid B [18]. After the accomplishment of the sequence, comparison of the 1 H NMR spectra of the synthesized compound with that of the natural product revealed that the peaks associated with the Serinol unit of the molecule were shifted significantly up field.…”

Achmatowicz reaction and its application in the syntheses of bioactive molecules

“…180 Tong and co-workers utilized an Achmatowicz reaction in the total synthesis of (+)-didemniserinolipid B ( 96 , Scheme 26) in 19 steps from commercially available materials. 108 In particular, the target compound was assembled from the 6,8-DOBCO system ( 97 ).…”