Total synthesis of pseudomonic acid C: application of the alkoxyselenation reaction in organic synthesis

Stereoselective Functionalization of Dihydropyran‐3‐ols: Application to the Synthesis of Enantiopure Ethyl Deoxymonate B

“…On the other hand, the 3,6‐ cis isomers 2 gave only the anti dihydroxylation products 9 with moderate‐to‐excellent yields (Table 4), showing parallel behavior to other structures with related substitution patterns described in the literature, which could also be accessible by this methodology, as will be described later 8…”

“…The required ketone 52b was obtained by oxidation of alcohol 50b (Scheme ) and then we explored the use of Horner–Wadsworth–Emmons conditions, previously used for related substrates. Unfortunately we were unable to improve on the results obtained for the isopropylidene series, and the reaction of 52b with the sodium anion of triethyl phosphonoacetate afforded 57 in low yield as an 80:20 mixture of E / Z isomers,8 which was used as a mixture in the next step. Although it is likely that these results could be improved through a thorough study of this step, at this point, the lack of time and material prevented us from achieving this goal and we decided to continue the sequence.…”

Recent Advances in the Chemistry and Biology of Naturally Occurring Antibiotics

“…The first total synthesis of pseudomonic acid C (144) was reported by Kozikowski and coworkers in 1980. [89] By 1995, at least fourteen total syntheses and formal total syntheses of pseudomonic acids had been published. These syntheses have been reviewed elsewhere.…”

Enantioselective Synthesis of Pseudomonic Acids. I. Synthesis of Key Intermediates

“…Meanwhile the structures of pseudomonic acids A (l), B (2) and C (3) have been elucidated [2-61. In spite of considerably growing interest in the synthesis of these antibiotic substances, as reflected by several recent reports on I and 3 [7][8][9][10][11][12], no approach to optically active compounds has been described so far. In addition, it should be noted that pseudomonic acid B (2 ) has not yet been the target molecule for synthetic studies at all.…”