Fig. 2 | Nature Communications

Fig. 2

From: Design and 22-step synthesis of highly potent D-ring modified and linker-equipped analogs of spongistatin 1

Fig. 2

Retrosynthetic analysis. The target molecules may be split into the ABCD* (6) and EF (7) fragments, which may be coupled with a Wittig reaction, followed by macrolactonization to complete the synthesis. A direct complex fragment coupling syn-crotylation reaction of 8 with CD* spiroketal aldehyde 9a or 9b was envisioned as the key step in the synthesis of the ABCD* fragment, while a direct complex fragment coupling alkallylation reaction of 10 with aldehyde 11 was envisioned as a critical step in the synthesis of the EF fragment. Crotyl- and allylsilanes 8 and 10 (M = Si) were envisioned to arise from diene 12 and allylchloride 13, greatly simplifying the synthesis. TFA trifluoroacetate, TMSE 2-trimethylsilylethyl, TES triethylsilyl, TBDPS tert-butyldiphenylsilyl, TBS tert-butyldimethylsilyl

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