910228-57-8

Upstream product

• 910228-56-7 (2R)-2-[(4S,5S)-5-ethyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]propan-1-ol 

Downstream Products

• 1009089-94-4 (2S,5E,7S)-1-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-7-[(4S,5S)-5-ethyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-2-[(1,1,1-triethylsilyl)oxy]-5-octen-4-one 
• 910228-58-9 C₂₁H₃₀O₅ 

Relevant academic research and scientific papers

Total synthesis of (-)-bitungolide F and determination of its absolute stereochemistry

(Chemical Equation Presented) A highly convergent total synthesis of bitungolide F leading to the assignment of its absolute stereochemistry is described. The key steps include a Horner-Wadsworth-Emmons olefination to construct the C7-C8 bond, a Wittig reaction to introduce the conjugate E,E-olefinic moiety in the molecule, and finally a ring-closing metathesis reaction to construct the six-membered α,β-unsaturated δ-lactone of the molecule. Modified Evans's syn-aldol reaction, using Crimmins's protocol, was used to install the stereochemistries at the C4 and C5 centers. The stereochemistry at C9 was introduced by means of hydroxy-directed reduction of the C9 keto using Evans's protocol.

Biomimetic synthesis of marine sponge metabolite spiculoic acid A and establishment of the absolute configuration of the natural product

The synthesis of spiculoic acid A (1) using a biomimetic Diels-Alder reaction is described; comparison of the specific rotation of the natural and synthetic material revealed that the enantiomer of the natural product has been synthesized. The Royal Socie