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Review
. 2023 Mar 17;28(6):2722.
doi: 10.3390/molecules28062722.

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

Aqsa Mushtaq  1 , Ameer Fawad Zahoor  1 , Muhammad Bilal  2 , Syed Makhdoom Hussain  3 , Muhammad Irfan  4 , Rabia Akhtar  1   5 , Ali Irfan  1 , Katarzyna Kotwica-Mojzych  6 , Mariusz Mojzych  7
Affiliations
Review

Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review

Aqsa Mushtaq et al. Molecules. .

Abstract

Sharpless asymmetric dihydroxylation is an important reaction in the enantioselective synthesis of chiral vicinal diols that involves the treatment of alkene with osmium tetroxide along with optically active quinine ligand. Sharpless introduced this methodology after considering the importance of enantioselectivity in the total synthesis of medicinally important compounds. Vicinal diols, produced as a result of this reaction, act as intermediates in the synthesis of different naturally occurring compounds. Hence, Sharpless asymmetric dihydroxylation plays an important role in synthetic organic chemistry due to its undeniable contribution to the synthesis of biologically active organic compounds. This review emphasizes the significance of Sharpless asymmetric dihydroxylation in the total synthesis of various natural products, published since 2020.

Keywords: Sharpless asymmetric dihydroxylation; alkaloids; enantioselective; flavones; lactones; macrolides; natural products; polyketides.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Osmium-catalyzed asymmetric dihydroxylation.
Figure 1
Figure 1
Structure of biologically important organic compounds employing Sharpless asymmetric dihydroxylation in their total synthesis.
Scheme 2
Scheme 2
Synthesis of (−)-zephyranthine 14.
Scheme 3
Scheme 3
Synthesis of epi-muscarine alkaloid 19.
Scheme 4
Scheme 4
Synthesis of alstolarines A 24 and B 25.
Scheme 5
Scheme 5
Synthesis of glyphaeaside C.
Scheme 6
Scheme 6
Synthesis of (−)-englerin A 39.
Scheme 7
Scheme 7
Synthesis of goyazensolide 43.
Scheme 8
Scheme 8
Synthesis of aromatic bisabolanes 49 and 51.
Scheme 9
Scheme 9
Synthesis of 4-epi-englerin A 58.
Scheme 10
Scheme 10
Synthesis of (−)-salvinorin A 67.
Scheme 11
Scheme 11
Synthesis of propindilactone G 75.
Scheme 11
Scheme 11
Synthesis of propindilactone G 75.
Scheme 12
Scheme 12
Synthesis of berkeleyone A 80 and preaustinoids 81, 82, 83 and 84.
Scheme 13
Scheme 13
Synthesis of trans-p-menth-3-ene-1,2,8-triol 88.
Scheme 14
Scheme 14
Synthesis of pladienolides 98.
Scheme 15
Scheme 15
Synthesis of alchivemycins A and B 103.
Scheme 16
Scheme 16
Synthesis of fostriecin 110.
Scheme 16
Scheme 16
Synthesis of fostriecin 110.
Scheme 17
Scheme 17
Synthesis of ascospiroketal B 118.
Scheme 18
Scheme 18
Synthesis of trichoderone A 127.
Scheme 19
Scheme 19
Synthesis of amphirionin-2 136.
Scheme 20
Scheme 20
Synthesis of (+)-PD-116740 144.
Scheme 21
Scheme 21
Synthesis of bryostatin 152.
Scheme 22
Scheme 22
Synthesis of zampanolide mimics 162.
Scheme 23
Scheme 23
Synthesis of formosalides A and B 169.
Scheme 24
Scheme 24
Synthesis of patulolide C 175.
Scheme 25
Scheme 25
Synthesis of tubuvaline 181.
Scheme 26
Scheme 26
Synthesis of alveolaride C 195.
Scheme 26
Scheme 26
Synthesis of alveolaride C 195.
Scheme 27
Scheme 27
Synthesis of new phenolic constituent 200.
Scheme 28
Scheme 28
Synthesis of DHPV 206 and 207.
Scheme 29
Scheme 29
Synthesis of sanjoseolide 212.
Scheme 30
Scheme 30
Synthesis of (+)-brazilin 220.
Scheme 31
Scheme 31
Synthesis of cudraisoflavone J 227.
Scheme 32
Scheme 32
Synthesis of FD-594 238.
Scheme 33
Scheme 33
Synthesis of D-xylulose 246.
Scheme 34
Scheme 34
Synthesis of 1,4-dideoxy-1,4-imino-D-iditol 256 and 257.
Scheme 35
Scheme 35
Synthesis of crisamicin 268.
Scheme 36
Scheme 36
Synthesis of EBC-23 274.
Scheme 37
Scheme 37
Synthesis of ieodomycins 282.
Scheme 38
Scheme 38
Synthesis of cardiobutanolide 293.
Scheme 39
Scheme 39
Synthesis of THF rings for caruifolin A 304.
Scheme 40
Scheme 40
Synthesis of C1-C16 fragment of formosalide B 312.
Scheme 41
Scheme 41
Synthesis of HIV-protease inhibitor 318.
Scheme 42
Scheme 42
Synthesis of (+)-muconin 329.
Scheme 43
Scheme 43
Synthesis of C14-C28 fragment of eribulin 338.
Scheme 44
Scheme 44
Synthesis of amphidinol 3 350.
Scheme 44
Scheme 44
Synthesis of amphidinol 3 350.
Scheme 45
Scheme 45
Synthesis of 4,5-dihydroxypiperines 354 and 355.
Scheme 46
Scheme 46
Synthesis of (+)-penostatins A 363 and C 364.
Scheme 47
Scheme 47
Synthesis of taxol side chain 368.
Scheme 48
Scheme 48
Synthesis of thuggacin cmc-A 378.
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