Zinc-Acetic Acid Reductive Cyclisation in a Two-Step Synthesis of the S1-N10 Nine-Membered Lactone Core of ent-Griseoviridin

Abstract

The synthesis of the S1-N10 nine-membered lactone core 28 of ent-griseoviridin is reported. Starting from cystine derivative 25, encompassing a terminal ynoate, treatment under Zn/AcOH conditions led to the formation of lactone 28 in 12% yield. Therefore, the lactone moiety of ent-griseoviridin is obtained in 10.7% overall yield for two steps. An access to the corresponding 5-epi-griseoviridin lactone 29 is also described.

Key words

lactones - antibiotics - reductions - cyclisations - griseoviridin

References

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14

X-ray crystallographic data, lists of refined coordinates and ESDs, of compound 29, are deposited at the Cambridge Crystallographic Centre.