51103-58-3

Basic information

• Product Name: SESQUICILLIN
• Synonyms: SESQUICILLIN;(9R)-3β-Acetoxy-13,15-dihydroxy-14,15-dimethyl-18-(3-methyl-2-butene-1-yl)-16-norlabda-8(17),12,14-triene-12-carboxylic acid δ-lactone;4-Hydroxy-3-[[(1R,4aR)-2-methylene-5α-(4-methyl-3-pentenyl)-6β-acetoxy-5,8aβ-dimethyldecahydronaphthalene]-1α-ylmethyl]-5,6-dimethyl-2H-pyran-2-one;Acetic acid (1S,8aα)-1,4aβ-dimethyl-6-methylene-1α-(4-methyl-3-pentenyl)-5α-(2-oxo-4-hydroxy-5,6-dimethyl-2H-pyran-3-ylmethyl)decalin-2β-yl ester;Sesquicillin A
• CAS NO: 51103-58-3
• Molecular Formula: C29H42O5
• Molecular Weight: 470.64
• Mol File: 51103-58-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: SESQUICILLIN(CAS DataBase Reference)
• NIST Chemistry Reference: SESQUICILLIN(51103-58-3)
• EPA Substance Registry System: SESQUICILLIN(51103-58-3)

Safety Data

• Hazardous Substances Data: 51103-58-3(Hazardous Substances Data)

Upstream product

• 1112232-55-9 ((1S,2S,4aR,5R,8aR)-5-((4-(methoxymethoxy)-5,6-dimethyl-2-oxo-2H-pyran-3-yl)methyl)-1,4a-dimethyl-6-methylene-1-(4-methylpent-3-enyl)decahydronaphthalen-2-yl) acetate 

Relevant articles and documents

Enantioselective total synthesis of novel diterpenoid pyrones (+)-sesquicillin and (-)-nalanthalide from fungal fermentations

We efficiently synthesized (+)-sesquicillin (a glucocorticoid antagonist) and (-)-nalanthalide (a potassium channel Kv1.3 blocker) in a convergent and unified manner starting from (+)-5-methyl-Wieland-Miescher ketone. The synthesis involved the following key steps: (i) a [2,3]-Wittig rearrangement of a stannylmethyl ether to install the stereogenic center at C9 and the exo-methylene functionality at C8 present in the tran/decalin portion, (ii) a coupling reaction of a trans-decalin portion with a γ-pyrone moiety to assemble the requisite whole carbon framework, and (iii) a conversion of a γ-pyrone moiety to an α-pyrone ring to produce (+)-sesquicillin. The present total synthesis has verified the absolute configuration of these natural products.

An efficient stereoselective total synthesis of DL-sesquicillin, a glucocorticoid antagonist

The key step in the total synthesis of sesquicillin (3) is a stereoselective Claisen rearrangement of 1 to afford 2. The synthesis also features an efficient sequence to install an α-pyrone moiety in a hindered environment; TBS = tert-butyldimethylsilyl.