Content of review 1, reviewed on July 04, 2024
In this manuscript, Bisai et al. attempted to achieve the first chemical synthesis of the aromatic tetraterpenoid selaginedorffone B using a biomimetic strategy. The key to their synthetic strategy lies in the intermolecular Diels-Alder dimerization reaction. The overall project was well-designed and executed, with encountered problems being resolved effectively. Despite the lengthy total synthetic steps, the overall synthetic sequence is relatively streamlined, which is commendable. However, the downside is that the authors did not obtain synthetic samples consistent with the natural product spectra. Admittedly, there may be issues with the structural identification of the target molecule. The authors also performed theoretical calculations on the dimerization Diels-Alder reaction, but these are not enough to compensate for the fact that the natural product was not synthesized. If the authors could focus on the stereochemistry of the monomers, the selectivity of the Diels-Alder dimerization (regioselective and endo/exo-selective) to ultimately synthesize and identify the target natural product, this reviewer would strongly recommend its publication in CS. Other suggestions for modifications are as follows:
1. I believe that "energy gap" is a better term than "energy difference" when describing the Diels-Alder reaction.
2. Delete the "see ester 10" in the sentence "Claisen rearrangement of 9 (see ester 10) followed by DIBAL-H reduction furnished aldehyde 11," please check this throughout the text.
3. Change "TMS-acetylene addition (see propargyl alcohol 12) followed by DMP" to "TMS-acetylene addition of 12 followed by..."
4. Replace "2 steps" with "two steps" in the text and related schemes.
5. Provide the structure of 21 in Scheme 2.
6. Change "Accordingly, compound 6 was charged for a sequential Mitsunobu reaction" to "compound 34 was charged for a sequential Mitsunobu reaction," please review the entire text for consistency.
Source
© 2024 the Reviewer.
Content of review 2, reviewed on July 18, 2024
Unfortunately, the author has not yet synthesized and identified the target natural product. Perhaps I should not demand this too much, as they have indeed synthesized the reported structure. In this sense, I agree with its publication in CS.
Source
© 2024 the Reviewer.
References
Sourav, K., Debgopal, J., Nilangshu, M., Ayan, M., Ranjit, M., Kishore, R. N., Ayan, D., Alakesh, B. 2024. Biomimetic total synthesis of the reported structure of (+)-selaginedorffone B. Chemical Science.
