Stereocontrol of 5-endo-trig cyclisations by hydroxyl groups: a formal short synthesis of (+)-muscarine

Knight, David W.; Staples, Emily R.

doi:10.1016/s0040-4039(02)01518-6

Cited by 17 publications

(5 citation statements)

References 14 publications

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“…When 2-(2-iodononyl)tetrahydrofuran ( 1a ), obtained as a single stereoisomer by the iodocyclization reaction of ( E )-4-methyl-4-tridecen-1-ol [ 6 , 7 , 8 , 9 , 10 , 11 , 12 ], was treated with DIT and acetic acid in a mixture of CH 2 Cl 2 and hexafluoroisopropanol (HFIP) at room temperature, the acetoxylated tetrahydropyran derivative 3a was obtained as a main product, along with an acetoxy group-substituted tetrahydrofuran derivative 5a as a minor product ( Table 1 , Entries 2–4). The use of HFIP as solvent was critical [ 13 ] and without it, the reaction was sluggish (Entry 1).…”

Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents

et al. 2005

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Stereoselective synthesis of 5-7 membered cyclic ethers was achieved by deiodonative ring-enlargement of cyclic ethers having an iodoalkyl substituent. The reaction took place readily under mild conditions using hypervalent iodine compounds and an acetoxy or a trifluoroacetoxy group was introduced into the rings depending on the hypervalent iodine reagent employed. The use of hexafluoroisopropanol (HFIP) as solvent is critical.

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Section: Resultsmentioning

confidence: 99%

Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents

et al. 2005

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“…Clearly, oxidation of the α-positions of the tetrahydrofuran ring takes precedence over cleavage of the phenyl group. Scheme 5 We therefore examined the prospects for employing a propargyl alcohol derivative, [48] and were glad to find that a non-chelation controlled addition [44] of lithiated O-TBDPS propargyl alcohol to O-silyl lactaldehyde 36 [43] gave the desired anti adduct 37 in excellent yield and with a very usable level of stereoselection (ca. 9:1 anti/syn) (Scheme 6).…”

Section: Resultsmentioning

confidence: 99%

Two Contrasting Asymmetric Approaches to Muscarine Based on 5‐endo‐trig Cyclisations

2004

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Keywords: Cyclisation / Muscarine / Oxygen heterocycles / Enantioselectivity / Natural products 5-endo-trig cyclisation of the (Z)-hydroxyalkenoate 17 using iodine as the electrophile gave a good yield of the β-hydroxytetrahydrofuran 18, probably via the corresponding iodohydrin. A variety of one-carbon degradation methods were then used to generate precursors to (−)-muscarine (25d). An alternative strategy featured control of a 5-endo-trig iodocyclisation by an allylic hydroxyl group, which can be used for the highly stereocontrolled synthesis of hydroxy-iodote-

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“…Knight and Staples applied their newly developed stereoselective cyclisation reaction to perform a short formal synthesis of 89 in 2002 (Scheme 12). 112 To prepare the required protected homoallylic alcohol 99, methyl (S)-lactate (98) was silyl-protected, reduced with diisobutylaluminum hydride and alkylated with a lithiated propargylic alcohol derivative. Addition of iodine monobromide initiated the cyclisation.…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of Secondary Metabolites from Higher Fungi

Reck

Spiteller

2015

Synthesis

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Higher fungi are a promising source of new bioactive natural products with great structural diversity, ranging from polyketides to terpenoids and alkaloids. Many of these structures are a challenge for synthetic organic chemists who have been inspired to develop new total syntheses. Nevertheless, reviews covering syntheses of fungal natural products are lacking. One aim of this review is to close this gap and to present a selection of more recent syntheses of fungal secondary metabolites from different structural classes. Secondly, this review intends to demonstrate that there are many more motivations for the synthesis of natural products than to confirm a proposed structure or to report the first total synthesis of a new natural product. Thirdly, this review is intended to stimulate the interest of organic chemists in the synthesis of fungal natural products. 1

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Stereocontrol of 5-endo-trig cyclisations by hydroxyl groups: a formal short synthesis of (+)-muscarine

Cited by 17 publications

References 14 publications

Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents

Stereoselective Synthesis of 5-7 membered Cyclic Ethers by Deiodonative Ring-Enlargement Using Hypervalent Iodine Reagents

Two Contrasting Asymmetric Approaches to Muscarine Based on 5‐endo‐trig Cyclisations

Synthesis of Secondary Metabolites from Higher Fungi

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