A photochemical C=C cleavage process: toward access to backbone N-formyl peptides

• Haopei Wang and
• Zachary T. Ball

Beilstein J. Org. Chem. 2021, 17, 2932–2938, doi:10.3762/bjoc.17.202

• unstable under basic conditions, readily forming aldehyde products 3. However, related hemi-aminal compounds are quite stable under non-basic conditions, and the motif is even contained in some natural products, such as zampanolide [21] and spergualin [22]. We propose a competing electrocyclization pathway

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

• Asha Budakoti,
• Pradip Kumar Mondal,
• Prachi Verma and
• Jagadish Khamrai

Beilstein J. Org. Chem. 2021, 17, 932–963, doi:10.3762/bjoc.17.77

• homoallylic alcohol 114 and aldehyde 115 in the presence of a catalytic amount of In(OTf)3 [61]. This approach was further used for the synthesis of a common intermediate 117 for (−)-zampanolide and (+)-dactyloide (Scheme 27) [62]. Further improvement of this reaction was achieved by carrying out the Prins

• ’ strategy for the synthesis of zampanolide and dactylolide. Loh and Chan’s strategy for THP synthesis. Prins cyclization of cyclohexanecarboxaldehyde. Prins cyclization of methyl ricinoleate (127) and benzaldehyde (88). AlCl3-catalyzed cyclization of homoallylic alcohol 129 and aldehyde 130. Martín and co

Preparation of conjugated dienoates with Bestmann ylide: Towards the synthesis of zampanolide and dactylolide using a facile linchpin approach

• Jingjing Wang,
• Samuel Z. Y. Ting and
• Joanne E. Harvey

Beilstein J. Org. Chem. 2015, 11, 1815–1822, doi:10.3762/bjoc.11.197

• products zampanolide and dactylolide is investigated using Bestmann ylide to link the C16–C20 alcohol with the C3–C8 aldehyde fragment. Keywords: Bestmann ylide; dactylolide; dienoate; (triphenylphosphoranylidene)ketene; zampanolide; Introduction (Triphenylphosphoranylidene)ketene, Ph3P=C=C=O (1), was

• structurally related marine natural products, zampanolide (2) and dactylolide (3, Figure 1), wherein the Bestmann ylide represents a C1–C2 linchpin that connects two segments of the macrocylic ring. (−)-Zampanolide (2, Figure 1) was first isolated from the marine sponge Fasciospongia rimosa found at Cape Zampa

• Dactylospongia [24] and has significantly lower cytotoxicity. The absolute configuration of the natural material is not firmly established due to discrepancies in optical rotation values between natural and synthetic samples [25]. Zampanolide and dactylolide have engendered world-wide interest from the synthetic