A convenient allylsilane- N-acyliminium route toward indolizidine and quinolizidine alkaloids

• Roland Remuson

Beilstein J. Org. Chem. 2007, 3, No. 32, doi:10.1186/1860-5397-3-32

• hydroxyalkylallylsilane 32 is accomplished in 40% yield following Trost's procedure. [48] Reaction of glutarimide with alcohol 32 under Mitsunobu reaction conditions afforded imide 33 in 67% yield. Reduction of 33 was carried out with an excess of sodium borohydride in methanol at 0°C to give 34 as a mixture of two

• , (-)-lasubine II and (+)-subcosine II A similar strategy was attempted from (+)-(3R)-ethyl 3-hydroxy-3-(3,4-dimethoxyphenyl)propionate but racemisation was observed during the Mitsunobu reaction. [69] So we developed another strategy to prepare these natural optically active compounds based on the

The use of silicon- based tethers for the Pauson- Khand reaction

• Adrian P. Dobbs,
• Ian J. Miller and
• Saša Martinović

Beilstein J. Org. Chem. 2007, 3, No. 21, doi:10.1186/1860-5397-3-21

• both for the formation of the silyl ethers and from the Pauson-Khand reaction were the corresponding silanols, we wondered if it would be possible to use these compounds for the preparation of our desired ethers via a Mitsunobu reaction. There are examples in the chemical literature in which silanols

• may be used analogously to alcohols in the Mitsunobu reaction.[29] Unfortunately, neither triisopropylsilanol (synthesised by the hydrolysis of commercially available triisopropylsilyl chloride) or diisopropyl(1-methylallyl)-silanol and but-2-enyldiisopropylsilanol gave any product and quantitative

ADDP and PS-PPh₃: an efficient Mitsunobu protocol for the preparation of pyridine ether PPAR agonists

• Paul S. Humphries,
• Quyen-Quyen T. Do and
• David M. Wilhite

Beilstein J. Org. Chem. 2006, 2, No. 21, doi:10.1186/1860-5397-2-21

• at the Mitsunobu reaction between pyridinol 2 and alcohol 3, utilizing a modification of the conditions originally reported by Mitsunobu,[18] afforded pyridyl ether 4 in 54% yield (Scheme 1). Interestingly, the reaction did not reach completion and pyridinol 2 was recovered, despite the fact that it

• Information File 1 and Supporting Information File 2]. With the above result in hand, we then pursued a variety of targets by performing the modified Mitsunobu reaction of 2 and a variety of primary alcohols (Table 1). In general, a variety of diverse alcohols afforded the expected products in excellent yield

• modified Mitsunobu coupling of pyridinols and alcohols proved to be versatile, efficient and amenable to parallel synthesis. A full account of the medicinal chemistry of these compounds will be given elsewhere. Thiazolidine-2,4-dione mimic & chosen lead scaffold. Proposed mechanism of the Mitsunobu

Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: Exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives

• Andrew Kennedy,
• Adam Nelson and
• Alexis Perry

Beilstein J. Org. Chem. 2005, 1, No. 2, doi:10.1186/1860-5397-1-2

• ] although the reducing agent still approaches the ketone from a pseudo-axial direction, the net stereochemical outcome is different (see Figure 6). The configuration of both alcohols in the bis-allylic alcohols trans-27 and cis-27 was cleanly inverted using a Mitsunobu reaction, and the resulting diesters